(2S,3R,4S,5S,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS No.: 97205-08-8
• Molecular Formula: C35H38 O5 S
• Molecular Weight: 570.75
• DSSTox Substance ID: DTXSID80471254
• Nikkaji Number: J755.888K
• Wikidata: Q82299724
• Mol file: 97205-08-8.mol

Synonyms:97205-08-8;(2S,3R,4S,5S,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane;Methyl 2,3,4,6-tetra-O-benzyl-a-D-thiogalactopyranoside;(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(methylthio)tetrahydro-2H-pyran;Methyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside;CTK8G0877;DTXSID80471254;W-204148

Chemical Property of (2S,3R,4S,5S,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane

Chemical Property:

• PSA: 71.45000
• LogP: 7.04730
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 14
• Exact Mass: 570.24399548
• Heavy Atom Count: 41
• Complexity: 684

Purity/Quality:

98% ^*data from raw suppliers

Methyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1C(C(C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: CS[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: Methyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside (CAS# 97205-08-8) is an oligosaccharide used in the synthesis of carbohydrates and macromolecules, such as in synthesis of triglycosylated rhamnoside fragment of rhamnogalacturonan-II side chain A.

Technology Process of (2S,3R,4S,5S,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane

There total 4 articles about (2S,3R,4S,5S,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.5%

benzyl bromide (100-39-0) + methyl 1-thio-β-D-galactopyranoside (155-30-6) → methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (97205-08-8,162061-34-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) 30 min, -5 deg C; 2.) 3 h, 10-20 deg C;

DOI:10.1016/0008-6215(87)80181-7

Reference yield:

per-O-benzylated methyl α-thiogalactopyranoside (160636-38-4,162061-34-9) → methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (97205-08-8,162061-34-9)

Guidance literature:

With iodine; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 20 - 24 ℃;

DOI:10.1016/S0957-4166(99)00501-7

Reference yield:

methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (55722-48-0) → methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (97205-08-8,162061-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 16 h / 20 °C

2: 91.5 percent / 1.) NaH / dimethylformamide / 1.) 30 min, -5 deg C; 2.) 3 h, 10-20 deg C

With sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)80181-7

upstream raw materials:

benzyl bromide

methyl 1-thio-β-D-galactopyranoside

per-O-benzylated methyl α-thiogalactopyranoside

methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

4-methoxyphenyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-galactopyranoside

2,3,4,6-tetra-O-benzyl-D-galactopyranose

per-O-benzylated methyl α-thiogalactopyranoside