152964-76-6

Basic information

• Product Name: ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-β-D-galactopyranoside
• Synonyms: ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-β-D-galactopyranoside
• CAS NO: 152964-76-6
• Molecular Weight: 494.652
• Mol File: 152964-76-6.mol

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-β-D-galactopyranoside(152964-76-6)
• EPA Substance Registry System: ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-β-D-galactopyranoside(152964-76-6)

Safety Data

• Hazardous Substances Data: 152964-76-6(Hazardous Substances Data)

Upstream product

• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 1381875-94-0 C₄₅H₅₂O₅SSi 
• 172275-99-9 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-galactopyranoside 
• 131564-36-8 ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 311797-15-6 ethyl 6-O-trityl-1-thio-β-D-galactopyranoside 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 311797-16-7 ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-β-D-galactopyranoside 
• 64-18-6 formic acid 
• 152964-71-1 ethyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 143995-72-6 ethyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 311797-23-6 methyl (2,3,4-tri-O-benzyl-α-D-galactopyranosyluronic acid)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 313360-61-1 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-1,2,5,6-tetra-O-acetyl-α,β-D-galactofuranose 
• 683210-93-7 (2S,4R)-4-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester 
• 311797-18-9 tert-butyl (ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranosid)uronate 

Relevant articles and documents

The effect of electron withdrawing protecting groups at positions 4 and 6 on 1,2-cis galactosylation

Ethyl 2,3,4-O-tribenzyl-6-O-chloroacetyl-1-d-thiogalactoside, phenyl 4,6-O-diacetyl-2,3-dibenzyl-1-d-thiogalactoside and phenyl 2,3-O-dibenzyl-4,6-O- dichloroacetyl-1-d-thiogalactoside were employed in the study of the stereoselectivity of the glycosylati

An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled.

Regio- and chemoselective reductive cleavage of 4,6-O-benzylidene-type acetals of hexopyranosides using BH3·THF-TMSOTf

Benzylidene-type cyclic acetals of carbohydrates undergo efficient reductive ring opening using BH3·THF and a catalytic amount of TMSOTf at room temperature. 4,6-O-Benzylidene-hexopyranosides afford the corresponding 4-O-benzyl ethers exclusive

Synthesis of homogalacturonan fragments

Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides α(1→4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the a(1''→4')-linked trimer 39 (48%). Approximately 8% of the β(1''→4')-coupled isomer was observed in the 13C NMR spectrum of the reaction mixture.

Synthesis of the Leishmania LPG core heptasaccharyl myo-inositol

Total synthesis of the core heptasaccharyl myo-inositol, Galp(α1-6)Galp(α1-3)Galf(β1-3)[Glcp(α1-PO4-6)Manp](α1-3)Manp(α1-4)GlcN p(α1-6)Ins-1-PO4, and the corresponding hexasaccharyl myo-inositol, Galp(α1-6)Galp(α1-3)Galf(β1-3)Manp(α1

PARTIAL SUBSTITUTION OF THIOGLYCOSIDES BY PHASE TRANSFER CATALYZED BENZOYLATION AND BENZYLATION

Partial substitution by phase transfer catalysis giving monobenzoylated and monobenzylated products from 2,3- and from 4,6-diols in ethyl 1-thio-D-hexopyranosides with the β-gluco, β-galacto- and α-manno-configurations are described.Two disaccharide thiog