(2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran
• CAS No.: 38184-10-0
• Molecular Formula: C40H41O5S
• Molecular Weight: 632.821
• Nikkaji Number: J790.248D
• Mol file: 38184-10-0.mol

Synonyms:38184-10-0;Phenyl 2,3,4,6-tetra-o-benzyl-1-thio-beta-d-glucopyranoside;(2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran;Phenyl 2,3,4,6-tetra-O-benzyl-b-D-thioglucopyranoside;(2R,3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane;(2R,3R,4S,5R,6S)-3,4,5-TRIS(BENZYLOXY)-2-[(BENZYLOXY)METHYL]-6-(PHENYLSULFANYL)OXANE;SCHEMBL1029965;BS-28238;A873908;W-202561;.Beta.-D-glucopyranoside,phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-

Chemical Property of (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

Chemical Property:

• PSA: 71.45000
• LogP: 8.47660
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 632.25964555
• Heavy Atom Count: 46
• Complexity: 798

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)SC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)SC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6
• Uses: Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (CAS# 38184-10-0) is a useful glycosylating agent and thioglycoside. Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside is used in the synthetic preparation of macromolecules such as mycobacterium tuberculosis nonasaccharide.

Technology Process of (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

There total 74 articles about (2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran 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: 98.0%

phenyl 1-thio-D-glucopyranoside (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) + benzyl bromide (100-39-0) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside (91602-61-8,38184-10-0,62774-37-2,74801-29-9,116501-52-1,116501-53-2,139974-84-8)

Guidance literature:

phenyl 1-thio-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; paraffin; at 0 ℃;

benzyl bromide; In N,N-dimethyl-formamide; paraffin; at 0 - 20 ℃;

DOI:10.3762/bjoc.8.46

Reference yield: 97.0%

thiophenol (108-98-5) + Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-59-2) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside (91602-61-8,38184-10-0,62774-37-2,74801-29-9,116501-52-1,116501-53-2,139974-84-8)

Guidance literature:

ytterbium(III) triflate; In acetonitrile; at 53 ℃; for 6h;

DOI:10.1016/S0040-4039(00)73563-5

Reference yield: 94.0%

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) + benzyl bromide (100-39-0) → phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jo900662v

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

benzyl chloride

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

diphenyldisulfane

Downstream raw materials:

cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Refernces

• 1、 Jensen, Henrik H.,Juul-Madsen, Line,Sandgaard, Tatjana L. P.,Trinderup, Helle H.. "Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation". . p. 4154 - 4167. Retrieved 2022/03/16.
• 2、 Bachmann, Thomas,Rychlik, Michael. "Chemical glucosylation of pyridoxine". . . Retrieved 2020/02/13.