Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside

Base Information

• Chemical Name: Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside
• CAS No.: 108032-93-5
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 440.471
• DSSTox Substance ID: DTXSID30451102
• Nikkaji Number: J1.314.024C
• Wikidata: Q72498841
• Mol file: 108032-93-5.mol

Synonyms:a-D-Mannopyranoside, phenyl1-thio-, tetraacetate (9CI)

Chemical Property of Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside

Chemical Property:

• Melting Point: 85°C(lit.)
• PSA: 139.73000
• LogP: 1.86180
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 440.11410351
• Heavy Atom Count: 30
• Complexity: 632

Purity/Quality:

97% ^*data from raw suppliers

Phenyl 2,3,4,6-tetra-O-acetyl-a-D-thiomannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)SC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)SC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: A mannose analog as inhibitors of a-mannosidas A mannose analog as inhibitors of α-mannosidase

Technology Process of Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside

There total 125 articles about Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-a-D-mannopyranoside 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%

thiophenol (108-98-5) + β-D-galactose peracetate (4163-60-4) → 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1021/acs.orglett.0c02692

Reference yield: 100.0%

phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside (911684-18-9) + 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) → 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 - 0 ℃;

DOI:10.1021/ja063247q

Reference yield: 99.0%

thiophenol (108-98-5) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.0833333h; sonication;

DOI:10.1021/jo060374w

upstream raw materials:

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

acetic anhydride

thiophenol

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

Downstream raw materials:

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

phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside

tetra-O-acetyl-1-O-methyl-β-D-glucopyranose

methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside