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

Base Information

• Chemical Name: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 77481-62-0
• Molecular Formula: C₁₂H₁₆O₅S
• Molecular Weight: 272.322
• Nikkaji Number: J1.614.472J
• Mol file: 77481-62-0.mol

Synonyms:Phenyl alpha-d-thiomannopyranoside;77481-62-0;Phenyl a-D-thiomannopyranoside;(2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triol;Phenyl--D-thio-mannopyranosid;SCHEMBL2484480;phenyl 1-thio-alpha-d-mannopyranoside;Phenyl alpha-D-thiomannopyranoside, 97%;W-203776

Chemical Property of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Melting Point: 126-131°C
• PSA: 115.45000
• LogP: -0.42140
• Storage Temp.: 2-8°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 272.07184478
• Heavy Atom Count: 18
• Complexity: 259

Purity/Quality:

97% ^*data from raw suppliers

Phenyl a-D-thiomannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)S[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Phenyl 1-Thio-α-D-mannopyranoside is a reagent in the synthesis of phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside by using benzylidene acetal-directed β-mannosylation.

Technology Process of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triol

There total 71 articles about (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triol 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: 100.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → (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)

Guidance literature:

With sodium methylate; at 0 ℃; for 0.166667h;

DOI:10.1016/0008-6215(95)00203-6

Reference yield: 100.0%

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → (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)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1007/s007060200016

Reference yield: 88.0%

thiophenol (108-98-5) + β-D-glucose pentaacetate (604-69-3) → (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)

Guidance literature:

thiophenol; β-D-glucose pentaacetate; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 6h;

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1002/chem.202002287

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

chloro-trimethyl-silane

phenylthiotrimethylsilane

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

Downstream raw materials:

β-phenylsulfanyl lactoside

methyl D-glucopyranoside

phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside

D-gluconic acid