Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 726173-66-6
• Molecular Formula: C₃₁H₃₁Cl₄NO₇
• Molecular Weight: 671.402
• Mol file: 726173-66-6.mol

Synonyms:Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

There total 3 articles about Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 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: 79.0%

trichloroacetonitrile (545-06-2) + 3,4,6-tri-O-benzyl-2-O-chloroacetyl-D-galactopyranose → Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (726173-66-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -30 ℃; for 4h;

DOI:10.1016/j.bmcl.2004.03.068

Reference yield:

3,4,5-tri-O-benzyl-D-galactopyranose (20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1) → Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (726173-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / pyridine / diethyl ether / 2 h / -10 - 25 °C

2: 85 percent / aq. NH₃ / tetrahydrofuran / 1 h

3: 79 percent / DBU / CH₂Cl₂ / 4 h / -30 °C

With pyridine; ammonium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.bmcl.2004.03.068

Reference yield:

3,4,6-tri-O-benzyl-1,2-O-dichloroacetyl-D-galactopyranose (726173-71-3) → Chloro-acetic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (726173-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / aq. NH₃ / tetrahydrofuran / 1 h

2: 79 percent / DBU / CH₂Cl₂ / 4 h / -30 °C

With ammonium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2004.03.068

upstream raw materials:

trichloroacetonitrile

3,4,5-tri-O-benzyl-D-galactopyranose

3,4,6-tri-O-benzyl-1,2-O-dichloroacetyl-D-galactopyranose

Downstream raw materials:

(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)]hexanoate tert-butyl ester

tert-butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-β-D-galactopyranosyloxy)hexanoate

tert-butyl (2S,5R)-2,6-diamino-5-[α-D-glucopyranosyl-(1->2)-β-D-galactopyranosyloxy]hexanoate

(2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-chloroacetyl-β-D-galactopyranosyloxy)hexanoate tert-butyl ester