106220-89-7

Basic information

• Product Name: Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside
• Synonyms: Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside;Methyl 6-O-benzyl-2,3-di-O-methyl-a-D-glucopyranoside;Methyl 2,3-di-O-methyl-6-O-(phenylmethyl)-alpha-D-glucopyranoside
• CAS NO: 106220-89-7
• Molecular Formula: C₁₆H₂₄O₆
• Molecular Weight: 0
• Mol File: 106220-89-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside(106220-89-7)
• EPA Substance Registry System: Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside(106220-89-7)

Safety Data

• Hazardous Substances Data: 106220-89-7(Hazardous Substances Data)

Upstream product

• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside 
• 130132-26-2 (3R,4S,5R,6S)-4,5,6-Trimethoxy-2-(2-phenyl-benzo[1,3]dithiol-2-yloxymethyl)-tetrahydro-pyran-3-ol 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside 
• 93-99-2 benzoic acid phenyl ester 

Downstream Products

• 111828-68-3 (2R,4R,5R,6S)-2-Benzyloxymethyl-4,5,6-trimethoxy-dihydro-pyran-3-one 
• 106220-90-0 ((2R,3R,4R,5R,6S)-2-Benzyloxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 
• 343776-55-6 (2R,3R,4S,5R,6S)-3-(2-{2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-2-benzyloxymethyl-4,5,6-trimethoxy-tetrahydro-pyran 
• 111828-70-7 (2R,3S,4R,5R,6S)-2-Benzyloxymethyl-3,4,5,6-tetramethoxy-3-methyl-tetrahydro-pyran 
• 111828-69-4 methyl 6-O-benzyl-2,3-di-O-methyl-4-C-methyl-α-D-galactopyranoside 
• 120333-22-4 methyl 6-O-benzyl-3,4-dideoxy-2-O-methyl-α-D-erythro-hex-3-enopyranoside 
• 120333-23-5 methyl 6-O-benzyl-4-deoxy-2,3-di-O-methyl-β-L-threo-hex-4-enopyranoside 
• 120333-18-8 (2R,3S,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran 
• 120333-26-8 (Z)-(2R,3S)-6-Benzyloxy-2,3-dimethoxy-hex-4-enal 
• 120333-21-3 6-O-benzyl-4,5-dideoxy-2,3-di-O-methyl-L-threo-hex-4-enose 
• 106221-16-3 (2R,4S,4aR,6S,7R,8S,8aS)-6,7,8-Trimethoxy-2-phenyl-4-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 106221-15-2 (2R,4R,4aR,6S,7R,8S,8aS)-6,7,8-Trimethoxy-2-phenyl-4-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 66728-83-4 methyl 2,3-di-O-methyl-4-O-p-methoxybenzyl-α-D-glucopyranoside 

Relevant articles and documents

Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides

A quick, efficient and convenient method for the regiospecific reductive ring opening of 4,6-O-benzylidene acetals of O-/S-alkyl/aryl glycosides of mono- and disaccharides, leading to the exclusive formation of the corresponding 6-O-benzyl ethers, using s

Hydrogenolysis of the 4,6-o-ketals of glucopyranosides. Configuration-dependent high regio- and stereo-selectivity of the diastereoisomeric acetophenone derivatives

Hydrogenolysis (reductive cleavage) of the (R) isomers of the acetophenone 4,6-O-derivatives of glucopyranosides with LiAlH4/AlCl3 gives the 4-O-(1′-phenylethyl) ethers with (R) configuration; the corresponding (5) isomers produce the respective (R) 6-O-(1′-phenylethyl) ethers are produced. The hydrogenolysis of other 4,6-O-ketals affords O 4 ether derivatives; the two diastereoisomeric 4,6-O-s-butylidene derivatives (cyclic ketals) give O 4-ethers with the opposite absolute configuration. The stereoselectivity of these reactions is explained by the development of a four-centre transition state. The absolute configuration of the ethers has been determined by means of circular dichroism measurements.

2-PHENYL-1,3-BENZODITHIOLYLIUM TRIFLUOROMETHANESULFONATE: A REAGENT FOR THE CONVERSION OF ALCOHOLS INTO BENZYL ETHERS AND BENZOATES UNDER MILD CONDITIONS.

2-Phenyl-1,3-benzodithiolylium trifluoromethanesulfonate, easily prepared from 1,2-benzenedithiol, converts alcohols into dithioorthoesters and ultimately, benzyl ethers (Bu3SnH) and benzoates (HgO/HBF4).

SYNTHESIS AND MASS SPECTRA OF 4-O-ACETYL-1,5-ANHYDRO-2,3,6-TRI-O-ETHYL-D-GLUCITOL AND THE POSITIONAL ISOMER OF 4-O-ACETYL-1,5-ANHYDRO-DI-O-ETHYL-O-METHYL-D-GLUCITOL AND 4-O-ACETYL-1,5-ANHYDRO-O-ETHYL-DI-O-METHYL-D-GLUCITOL

Reductive cleavage of fully methylated, partially O-ethylated cellulose or fully ethylated, partially O-methylated cellulose and subsequent acetylation had previously been shown to produce 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-, -6-Oethyl-2,3-di-O-methyl-, -3-O-ethyl-2,6-di-O-methyl-, -2-O-ethyl-3,6-di-O-methyl-, -2,3,di-O-ethyl-6-O-methyl-, -2,6-di-O-ethyl-3-O-methyl-, -3,6-di-O-ethyl-2-O-methyl-, and -2,3,6-tri-O-ethyl-D-glucitol.Described herein is the independent synthesis of these derivatives, except for the first (which had been reported); and their (1)H-n.m.r. spectra, chemical-ionization (NH3) mass spectra, and electron-impact mass spectra are tabulated.

ON THE COMMUNICATION OF CHIRALITY FROM FURANOSE AND PYRANOSE RINGS TO MONOSACCHARIDE SIDE CHAINS: ANOMALOUS RESULTS IN THE GLUCOSE SERIES

The reactions of allyltrimethylsilane with dialdose derivatives occur, under catalysis by boron trifluoride etherate or titanium tetrachloride, with high stereoselectivity, thereby providing simple routes to the corresponding allyl carbinols.The sense of