3359-36-2

Upstream product

• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 100-51-6 benzyl alcohol 
• 643-17-4 α-D-rhamnopyranose 
• 1187858-70-3 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 108-24-7 acetic anhydride 
• 251361-11-2 benzyl L-rhamnopyranoside 
• 73-34-7 L-rhamnose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 122089-71-8 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 
• 3359-35-1 (2R,3R,4R,5R,6S)-2-benzyloxy-tetrahydro-6-methyl-2H-pyran-3,4,5-triol 

Downstream Products

• 53270-14-7 benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 26623-27-8 benzyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 26623-26-7 benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose 
• 88818-98-8 benzyl 4-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 88819-02-7 benzyl-3-O-allyl-4-O-benzyl-6-deoxy-α-L-talopyranoside 
• 88830-28-8 benzyl 3,4-di-O-benzyl-6-deoxy-2-O-methyl-α-L-talopyranoside 
• 88819-07-2 benzyl 2-O-benzoyl-4-O-benzyl-6-deoxy-α-L-talopyranoside 
• 88819-05-0 benzyl 2-O-allyl-3-O-benzoyl-6-deoxy-α-L-talopyranoside 
• 88819-06-1 benzyl 3-O-allyl-2-O-benzoyl-6-deoxy-α-L-talopyranoside 
• 88819-09-4 benzyl 2,3-di-O-benzoyl-4-O-benzyl-6-deoxy-α-L-talopyranoside 
• 88830-29-9 benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-talopyranoside 
• 88819-16-3 benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-talopyranoside 
• 88818-92-2 benzyl 6-deoxy-α-L-talopyranoside 
• 88818-91-1 benzyl 4-O-acetyl-6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 

Relevant academic research and scientific papers

A Unified Strategy to Access 2- And 4-Deoxygenated Sugars Enabled by Manganese-Promoted 1,2-Radical Migration

The selective manipulation of carbohydrate scaffolds is challenging due to the presence of multiple, nearly chemically indistinguishable O-H and C-H bonds. As a result, protecting-group-based synthetic strategies are typically necessary for carbohydrate modification. Here we report a concise semisynthetic strategy to access diverse 2- and 4-deoxygenated carbohydrates without relying on the exhaustive use of protecting groups to achieve site-selective reaction outcomes. Our approach leverages a Mn2+-promoted redox isomerization step, which proceeds via sugar radical intermediates accessed by neutral hydrogen atom abstraction under visible light-mediated photoredox conditions. The resulting deoxyketopyranosides feature chemically distinguishable functional groups and are readily transformed into diverse carbohydrate structures. To showcase the versatility of this method, we report expedient syntheses of the rare sugars l-ristosamine, l-olivose, l-mycarose, and l-digitoxose from commercial l-rhamnose. The findings presented here validate the potential for radical intermediates to facilitate the selective transformation of carbohydrates and showcase the step and efficiency advantages attendant to synthetic strategies that minimize a reliance upon protecting groups.

Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates

Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the es

Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger

A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.

Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates

A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, g

Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.

InCl3.3H2O: An efficient Lewis acid catalyst for stereoselective O-glycosidation reactions of per-O-acetylglycopyranosyl trichloroacetimidates

InCl3.3H2O catalysed highly stereoselective O-glycosidation of per-O-acetylglycopyranosyl trichloroacetimidates with a variety of aliphatic alcohols in dichloromethane at room temperature furnishes the corresponding glycosides in very good yields with excellent 1,2-trans stereoselectivity.

Syntheses of spacer-armed carbohydrate components of the Mycobacterium avium serocomplex serovar 8

p-Nitrophenyl glycosides of 3-O-Me-β-D-Glcp-(1 → 3)-α-L-Rhap, α-L-Rhap-(1 → 2)-6-deoxy-α-L-Talp, and 3-O-Me-β-D-Glcp-(1 → 3)-α-L-Rhap-(1 → 2)-6-deoxy-α-L-Talp have been prepared, related to Mycobacterium avium. Various glycosylation methods have been used

SYNTHESIS OF ALLYL AND BENZYL 4-O-(3,6-DI-O-METHYL-β-D-GLUCOPYRANOSYL)-2,3-DI-O-METHYL-α-L-RHAMNOPYRANOSIDE

Condensation of 2,4-di-O-acetyl-3,6-di-O-methyl-α-D-glucopyranosyl bromide with either allyl or benzyl 2,4-di-O-methyl-α-L-rhamnopyranoside in the presence of mercuric cyanide, followed by O-deacetylation, gave the title oligosaccharides in excellent yiel

DERIVATIVES OF 6-DEOXY-L-TALOSE AND THE SYNTHESIS OF 6-DEOXY-2-O-(α-L-RHAMNOPYRANOSYL)-L-TALOSE

Benzyl 6-deoxy-α-L-talopyranoside (10) has been synthesized and provides, after hydrogenolysis, an improved preparation of 6-deoxy-L-talose.Several partially substituted derivatives of the glycoside 10 have been prepared, including benzyl 6-deoxy-3,4-O-is