106445-04-9

Upstream product

• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 177897-32-4 Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 
• 888954-88-9 methanesulfonic acid (6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethyl ester 
• 444118-89-2 pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 525593-61-7 pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 444118-90-5 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 
• 444118-91-6 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 
• 444118-88-1 pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 106445-09-4 (S)-4-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-dihydro-furan-2-one 
• 106445-08-3 (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-butyric acid methyl ester 
• 94393-44-9 (S)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol 
• 94393-43-8 (2R,3R)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol 
• 106445-11-8 (R)-4-[(R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[1,3]dioxolane-2-thione 
• 94393-42-7 (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol 
• 106499-05-2 (Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-en-1-ol 

Relevant academic research and scientific papers

An unexpected migration of O-silyl group under Mitsunobu reaction conditions

A 1,4 O→O silyl migration followed by nucleophilic substitution with phthalimide was observed under Mitsunobu reaction conditions. This one step secondary alcohol protection and primary alcohol substitution with N-nucleophiles was extended to a variety of

A short and simple synthesis of 1-deoxynojirimycin derivatives from D-glucose

Insertion of an amino functionality at C-5 of D-glucose with inversion of configuration, followed by imine formation with the latent aldehyde at C-1 and concomitant reduction furnished the 1-deoxynojirimycin skeleton. Georg Thieme Verlag Stuttgart.

Modular synthesis of heparin oligosaccharides

A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti

Highly stereoselective indium trichloride-catalysed asymmetric aldol reaction of formaldehyde and a glucose-derived silyl enol ether in water

The yield and stereochemical outcome of the reaction between D-glucose-derived silyl enol ether 1 (Z and E isomers) and commercial formaldehyde in water catalysed by indium(III) choride was studied.

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).

Zaragozic acid a : Interesting observations in anhydro-ring formation of densely functionalised carbohydrate templates

A methodology which produced highly substituted 1,6-anhydrofuranose derivative, symbolising 2,8-dioxobicyclo[3.2.1]octan core of zaragozic acid, has been described.

A formal synthesis of a novel immunosuppressant ISP-1 : Stereocontrolled Pd(O) catalysedcis-hydroxyamination of carbohydrate derived vinyl epoxide

Described herein are the results leading to the synthesis of ISP-1 containing an unusal α, α-disubstituted amino acid and whose immunosuppressive activity only has recently been discovered.

SYNTHESES OF PSEUDO-α-D-GLUCOPYRANOSE AND PSEUDO-β-L-IDOPYRANOSE, TWO OPTICALLY ACTIVE PSEUDO-HEXOPYRANOSES, FROM D-GLUCOSE BY USING STEREOSELECTIVE REDUCTIVE DEACETOXYLATION WITH SODIUM BOROHYDRIDE AND CYCLITOL FORMATION FROM NITROFURANOSE AS KEY REACTIO

Two optically active pseudo-hexopyranoses, pseudo-α-D-glucopyranose and pseudo-β-L-idopyranose, have been synthesized from D-glucose by using stereoselective deacetoxylations with NaBH4 and cyclitol formations from nitrofuranose derivatives as key reactio

1,3,5-TRIDEOXY-3,5-DI-C-METHYL-L-TALITOL: A CHIRON FOR THE C-33-C-37 SEGMENT OF AMPHOTERICIN B

1,3,5-Trideoxy-3,5-di-C-methyl-L-talitol is a potential chiron for the C-33-C-37 segment of amphotericin B.This hexitol has been synthesized from 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose by a route in which a C-methylene derivative at C-5 is hydr