Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside
• CAS No.: 187022-49-7
• Molecular Formula: C₂₁H₂₄Cl₃NO₉S
• Molecular Weight: 572.848
• Mol file: 187022-49-7.mol

Synonyms:(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property of Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 143°C(lit.)
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-β-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside

There total 14 articles about Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-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: 98.0%

thiophenol (108-98-5) + 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (187022-27-1) → (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate (187022-49-7)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 40 ℃;

DOI:10.1016/S0008-6215(96)90118-4

Reference yield: 89.0%

thiophenol (108-98-5) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9) → (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate (187022-49-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1248/cpb.45.312

Reference yield: 70.0%

O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate (136945-14-7) + (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol (675876-42-3) → (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate (187022-49-7) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4R,5R,6S)-5-azido-3-benzyloxy-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (676227-84-2)

Guidance literature:

With boron trifluoride diethyl etherate; at -78 ℃;

DOI:10.1016/j.tetlet.2003.12.042

upstream raw materials:

thiophenol

4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

(+)-D-glucosamine hydrochloride

Downstream raw materials:

N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside

N-(tert-butoxycarbonyl)-glycyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranosyl]-L-serine benzyl ester

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide

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