87316-22-1

Basic information

• Product Name: 6-O-(TERT-BUTYLDIPHENYLSILYL)-D-GLUCAL
• Synonyms: 6-O-(TERT-BUTYLDIPHENYLSILYL)-D-GLUCAL;(2R,3S,4R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-3,4-diol
• CAS NO: 87316-22-1
• Molecular Formula: C₂₂H₂₈O₄Si
• Molecular Weight: 418.56
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 87316-22-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: −9 °C(lit.)
• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: 6-O-(TERT-BUTYLDIPHENYLSILYL)-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(TERT-BUTYLDIPHENYLSILYL)-D-GLUCAL(87316-22-1)
• EPA Substance Registry System: 6-O-(TERT-BUTYLDIPHENYLSILYL)-D-GLUCAL(87316-22-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 87316-22-1(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 21193-75-9 D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 25878-60-8 D-galactose pentaacetate 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 137792-66-6 phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-D-galactal 
• 142800-29-1 (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-((3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-3-ol 
• 142800-28-0 (4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose 
• 124067-17-0 (2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol 
• 151797-32-9 3,4-di-O-acetyl-6-O-(tert-butyl diphenylsilyl)-D-glucal 
• 137792-57-5 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-glucal 
• 131156-53-1 (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol 
• 131156-53-1 (2R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol 
• 151265-18-8 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 
• 142865-32-5 (6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose 
• 220931-00-0 3-O-(1,3-Diphenylprop-2-en-1-yl)-6-O-t-butyldiphenylsilyl-D-glucal 
• 193360-22-4 (2R,3S,4R)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-ol 
• 201800-34-2 3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal 
• 336130-11-1 1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose 

Relevant articles and documents

2-nitroglycal and efficient synthesis method thereof

The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.

Method for stereoselectively synthesizing beta-2-deoxyglycoside bond

The invention discloses a method for stereoselectively synthesizing a beta-2-deoxyglycoside bond. The method comprises the following steps: performing glycosylation on 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene serving as a donor, a saccharide receptor and a molecular sieve under the condition of the existence of an accelerant, wherein an isopropyl acetal protectivegroup is mounted on a 3-site hydroxyl and a 4-site hydroxyl of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene and a TBDPS is mounted on the 6-site of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene; through the synergistic effect of the protective groups, sugar ring conformation of the donor is controlled, and the stereoselective synthesis of a beta-configuration is realized. According to the method, the stereoselectivity of the glycosylation can be controlled effectively and stereoselectively; the method is wide in substrate application range and convenient to operate; raw materials are easy to obtain; side reactions of the glycosylation are few; a target product is high in yield and optical purity; a new design thought is provided for the research of the glycosylation.

Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl β-O-glycosides

Arylation of 6-O-tert-butyldiphenylsilyl-3,4-di-O-isobutyloxycarbonyl-d-glucal (3) with various phenols in the presence of a catalytic amount of palladium(0) gave the corresponding 2,3- and 3,4-unsaturated β-O-glycosides. The reaction is stereospecific, i