16848-76-3

Usage

InChI:InChI=1/C14H18O4/c1-15-13-8-7-11-12(17-13)9-16-14(18-11)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3

Upstream product

• 132074-89-6 methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-threo-hex-2-enoside 
• 132074-90-9 methyl 4,6-O-benzylidene-2,3-di-O-[(methylthio)thiocarbonyl]-α-D-galactopyranoside 
• 1373344-40-1 C₂₁H₂₂O₆S 
• 221662-13-1 methyl 2-deoxy-4,6-O-benzylidene-α-D-galactopyranoside 
• 21193-75-9 D-galactal 
• 3169-98-0 methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 4234-42-8 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-ribohexopyranosid-3-ulose 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 688-73-3 tri-n-butyl-tin hydride 
• 145260-42-0 C₂₈H₂₆O₈S₂ 
• 6698-32-4 methyl 4,6-O-benzylidene-2-O-toluene-p-sulfonyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 

Downstream Products

• 131985-35-8 methyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-threo-hexopyranoside 
• 132023-36-0 (4R,5R)-4,6-dibenzyloxy-5-p-toluenesulfonyloxyhexanal ethylene dithioacetal 
• 131985-39-2 (4R,5S)-5-azido-4,6-dibenzyloxyhexanal ethylene dithioacetal 
• 131985-38-1 2-mercaptoethyl 4,6-di-O-benzyl-1-thio-1,2,3-trideoxy-α-D-threo-hexoside 
• 131985-40-5 (4R,5S)-5-azido-4,6-dibenzyloxyhexanal 
• 131985-37-0 (4R,5R)-4,6-dibenzyloxy-5-hydroxyhexanal ethylene dithioacetal 

Relevant academic research and scientific papers

Bromodimethylsulfonium bromide catalyzed synthesis of methyl 2-dexoy-4,6-o-benzylidene galactopyranoside from galactal and the rapid route to 2,3- and 2,6-dideoxygalactopyranoses

4,6-O-Benzylidenation of D-galactal with PhCH(OCH3)2 catalyzed by bromodimethylsulfonium bromide leads to methyl 2-dexoy-4,6-O- benzylidene galactopyranoside efficiently, which serves as a key intermediate to the ready preparation of

Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols

(Chemical Equation Presented) We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarbonyl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity.

The Synthesis of (2S,3R)-2-Hydroxymethylpiperidin-3-ol, a Fragment of the Alakloid Swainsonine

Methyl α- and β-D-galactopyranoside have been converted into methyl 4,6-di-O-benzyl-2,3-dideoxy-α- and -β-D-threo-hexoside, and subsequent treatment with ethanedithiol gives the same alcohol.Tosylation and azide displacement gives, after hydrolysis, an az

SYNTHESIS AND STEREOCHEMICAL CHARACTERIZATION OF OPTICALLY ACTIVE 2-METHOXY-3,4-DIHYDRO-2H-PYRAN

Samples of (+)-2-methoxy-3,4-dihydro-2H-pyran (1) have been prepared starting from methyl α-D-glucopyranoside and from tri-O-acetyl-D-glucal; the absolute configuration as well as the maximum rotatory power of 1 have been established.

An investigation of the Kishner elimination as a route to dideoxy sugars

Methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-ribohexopyranosid-3-ulose has been used as a substrate for an investigation of the Kishner elimination as a route to deoxygenated sugars.The conditions of the reaction of the ketotosylate with hydrazine

Process for deoxygenating secondary alcohols

The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100° C and under an inert atmosphere. The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity. Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.