58479-62-2

Basic information

• Product Name: (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol
• Synonyms: (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol
• CAS NO: 58479-62-2
• Molecular Weight: 432.589
• Mol File: 58479-62-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol(58479-62-2)
• EPA Substance Registry System: (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol(58479-62-2)

Safety Data

• Hazardous Substances Data: 58479-62-2(Hazardous Substances Data)

Usage

General Description

The chemical compound (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol is a complex molecule with a tetrahydro-pyran structure and several functional groups. It contains a tert-butyl-diphenyl-silanyloxymethyl group, a methoxy group, and three hydroxyl groups. (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol has potential applications in the pharmaceutical and chemical industries due to its unique structure and potential biological activity. The specific stereochemistry and functional groups present in this compound can affect its properties and potential uses in various fields.

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 154859-16-2 <2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-di-(2-oxoethyl)octahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 58479-67-7 methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 

Downstream Products

• 148657-21-0 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-glucopyranoside 
• 145149-86-6 O-(6-O-Acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-1-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranose 
• 153541-58-3 1-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 441018-00-4 Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-iodo-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester 
• 503173-63-5 1-O-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 1451062-73-9 (6-O-tert-butyl-diphenylsilyl)-methyl-α-D-ribo-hexapyranoside-3-ulose 
• 496849-16-2 methyl-3-amino-α-D-ribo-hexapyranoside 
• 154859-12-8 <2'R,2''R,6'R,6''R> methyl 4-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 154859-14-0 <2'R,2''R,6'R,6''R> methyl 4-O-acetyl-6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 154859-16-2 <2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-di-(2-oxoethyl)octahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 21056-51-9 methyl 4-O-benzoyl-α-D-glucopyranoside 
• 4201-66-5 methyl 6-O-acetyl-α-D-glucopyranoside 
• 189825-44-3 {(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester 
• 210159-35-6 methyl 2,3,4-tris-O-(p-bromobenzoyl)-α-D-glucopyranoside 

Relevant articles and documents

Synthesis of amphiphilic A3B mikto-arm copolymers from a sugar core: Combination of hydrophobic PCL and hydrophilic glycopolymers for biocompatible nanovector preparation

Amphiphilic A3B mikto-arm copolymers have been synthesized using a t-butyl-diphenyl silyl-based methylglucoside derivative. The latter has been first used as initiator for the polymerization of ε-caprolacto ne leading to three-arm starshaped st

Application of ball milling technology to carbohydrate reactions: I. Regioselective primary hydroxyl protection of hexosides and nucleoside by planetary ball milling

Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.

Imidazole-promoted 1,4-migration of the tert-butyldiphenylsilyl group: Influence on the selectivity control of the silylation reactions of carbohydrate OH groups

The regioselective protection of secondary hydroxy groups of gluco-, galacto-, manno-, rhamno- and fucopyranosides using TBDPSCl with imidazole in DMF has been studied. It was found that the relative spatial arrangement of the OH groups modulates the silylation selectivity which arises from the combination of kinetic factors and the intramolecular migrations of the secondary TBDPS groups. The rearrangement of the TBDPS groups has a much larger effect on the α-D-manno- and α-L-rhamnopyranosides, allowing the protection of the OH groups at positions 2, 3 or 2 and 4, in synthetically useful yields, by changing the reaction conditions. The relative reactivity of the secondary OH groups seems particularly likely to be governed by steric factors. This trend provides a valuable approach to the synthesis of 3-O-tert-butyldiphenylsilyl-1-thio-β-L-fucopyranoside.