PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 23661-28-1
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 440.471
• Hs Code.: 29329990
• Nikkaji Number: J1.036.457D
• Mol file: 23661-28-1.mol

Synonyms:Glucopyranoside,phenyl 1-thio-, tetraacetate (7CI); Glucopyranoside, phenyl 1-thio-,tetraacetate, b-D-(8CI); b-D-Glucopyranoside, phenyl1-thio-, tetraacetate (9CI); NSC 129250; Phenyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-glucopyranoside

Chemical Property of PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Appearance/Colour: WHITE TO YELLOW POWDER, CRYSTALS CRYSTALLINE POWDER AND/OR CHUNKS
• Vapor Pressure: 1.06E-10mmHg at 25°C
• Melting Point: 116-119 °C(lit.)
• Boiling Point: 514.6 °C at 760 mmHg
• Flash Point: 247.6 °C
• PSA: 139.73000
• Density: 1.31 g/cm³
• LogP: 1.86180
• Storage Temp.: Freezer
• Solubility.: slightly sol. in Chloroform
• 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:

98%, ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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

Technology Process of PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE

There total 125 articles about PHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE 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:

2-(trimethylsilyl)ethyl 2-zido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

4-methylumbelliferyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>3)-2-O-benzyl-4,6-benzylidene-β-D-glucopyranoside

2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate

Refernces

• 1、 Wu, Hongxiang,Zhang, Yiwei,Li, Yuanxin,Xu, Jianchao,Wang, Yu,Li, Xuechen. "Chemical Synthesis and Biological Evaluations of Adiponectin Collagenous Domain Glycoforms". supporting information. p. 7808 - 7818. Retrieved 2021/05/26.
• 2、 Krumb, Matthias,J?ger, Maximilian,Voss, Alice,Immig, Loreen,Peters, Karin,Kowalczyk, Danuta,Bufe, Albrecht,Opatz, Till,Holst, Otto,Vogel, Christian,Peters, Marcus. "Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention". supporting information. p. 928 - 933. Retrieved 2020/10/29.