Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside
• CAS No.: 197005-22-4
• Molecular Formula: C21H26 O8 S
• Molecular Weight: 438.49
• Mol file: 197005-22-4.mol

Synonyms:Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside

Chemical Property of Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 113.0 to 117.0 °C
• Refractive Index: 1.547
• Boiling Point: 533.22°C at 760 mmHg
• Flash Point: 258.678°C
• PSA: 122.66000
• Density: 1.253g/cm³
• LogP: 2.50130

Purity/Quality:

98% ^*data from raw suppliers

Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-1-thio-beta-D-glucopyranoside

There total 3 articles about Phenyl 2,4,6-Tri-O-acetyl-3-O-allyl-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: 82.0%

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside (39698-00-5) + thiophenol (108-98-5) → phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside (197005-22-4,1820572-28-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1007/s007060200016

Reference yield:

(3aR,5S,6aR)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol → phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside (197005-22-4,1820572-28-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / NaH / dimethylformamide

2.1: amberlite IR-120 H / methanol

2.2: 98 percent / DMAP / pyridine

3.1: 82 percent / BF₃OEt₂ / CH₂Cl₂

With amberlite IR-120 H; boron trifluoride diethyl etherate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1007/s007060200016

Reference yield:

(3aR,5R,6aR)-6-Allyloxy-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside (197005-22-4,1820572-28-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: amberlite IR-120 H / methanol

1.2: 98 percent / DMAP / pyridine

2.1: 82 percent / BF₃OEt₂ / CH₂Cl₂

With amberlite IR-120 H; boron trifluoride diethyl etherate; In methanol; dichloromethane;

DOI:10.1007/s007060200016

upstream raw materials:

acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside

thiophenol

Downstream raw materials:

phenyl 3-O-allyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside

phenyl 3-O-allyl-1-thio-β-D-glucopyranoside

phenyl 3-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Succinic acid mono-[(2R,3R,4R,5R,6S)-4-allyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl] ester

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