Comments on: Reactions of Sugars: Glycosylation and Protection https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/ Mon, 19 Sep 2022 15:40:09 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-634564 Wed, 03 Aug 2022 20:45:55 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-634564 In reply to Ananaya.

The C1 carbon is not primary; it’s a hemiacetal (a masked aldehyde)

The OH on C-6 is significantly farther away from the rest of the molecule than any of the other OH groups, including the hemiacetal on C1, making it considerably more reactive towards a bulky protecting group like the trityl anion

]]> By: Darshan Joshi https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-602132 Thu, 10 Jun 2021 09:12:47 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-602132 when glucose reacts with hno3 , then (considering Fischer structure of glucose) only the aldehyde group and lowermost alcohol group in the structure gets oxidized to produce saccharic acid. so my question is , why won’t other alcohol groups in the structure of glucose get oxidized

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-598986 Mon, 22 Mar 2021 15:23:00 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-598986 In reply to Sara.

No, you really need a very bulky protecting group like trityl or even tri-isopropylsilyl(TIPS) will also do the job. Tosyl and mesyl and triflyl are not selective enough; they’ll hit everything. I don’t recommend using Tf, as OTf is a *great* leaving group and you’ll likely get a mess.

]]> By: Sara https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-598781 Tue, 16 Mar 2021 13:37:13 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-598781 Hello James, awesome topic!! My question is about Mesylation/Tosylation or even using Tf2O. Are they still selective on OH-6 like trityl group?

]]> By: Ananaya https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-585715 Wed, 07 Oct 2020 09:24:26 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-585715 In the attack of bulky substituent how u took the primary alcohol of C6 as C1 carbon is also having primary oh group as the oh attached to C1 is further jst attached to C2 i.e one alkyl so it’s primary na????

]]> By: Shreya Shah https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-578940 Thu, 09 Apr 2020 10:37:42 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-578940 What if you an acetal coming off the sugar other than the actual acetal involved in a glycosidic linkage, then can you hydrolyze that acetal?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-561963 Wed, 28 Aug 2019 02:18:22 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-561963 In reply to Momen.

In the absence of any acid or other reagent, the most exciting thing that can happen is that you form a hemiacetal between one of the glucose hydroxyls and the aldehyde of vanillin. Not very exciting.

]]> By: Momen https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-561618 Sun, 25 Aug 2019 02:58:54 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-561618 Dear James, thanks for your efforts. I would like to ask you if we react vanillin with D glucose. What should happen?

]]> By: Christoffer https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-542585 Wed, 07 Nov 2018 06:31:01 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-542585 Hey James
love your site
What would happen if you reacted d-glucose with R-SH, so a thiol, in acid? d-glucose with two S-R where the carbonyl oxygen was?

]]> By: James https://www.masterorganicchemistry.com/2018/04/24/reactions-of-sugars-glycosylation-and-protection/#comment-531541 Thu, 26 Apr 2018 16:20:15 +0000 https://www.masterorganicchemistry.com/?p=11455#comment-531541 In reply to Nick.

I most certainly am not, but if you found this article useful, I’m glad.

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