.alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate

Base Information

• Chemical Name: .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate
• CAS No.: 13992-16-0
• Molecular Formula: C20H24 O9 S
• Molecular Weight: 440.471
• Mol file: 13992-16-0.mol

Synonyms:Glucopyranoside,phenyl 1-thio-, tetraacetate, a-D- (8CI)

Chemical Property of .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate

Chemical Property:

• Melting Point: 85-87°C
• Boiling Point: 514.6±50.0 °C(Predicted)
• PSA: 139.73000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 1.86180
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Phenyl-2,3,4,6-tetra-o-acetyl-1-thio-alpha-D-mannopyranoside 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate

There total 142 articles about .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate 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:

phenyl-1-thio-α-D-glucopyranoside

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

α-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-galactopyranose

1-thiophenyl-β-D-galactopyranoside

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.