Chloro-acetic acid (3R,4S,5R,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 (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:250273-52-0
Molecular Formula:C₃₁H₃₁Cl₄NO₇
Molecular Weight:671.402
Hs Code.:

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

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

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

There total 4 articles about Chloro-acetic acid (3R,4S,5R,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: 90.0%

: 545-06-2
trichloroacetonitrile

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

: 250273-52-0
Chloro-acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -30 ℃; for 0.5h;
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 250273-52-0
Chloro-acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / OsO₄; 4-methylmorpholine oxide; H₂O / acetone; 2-methyl-propan-2-ol / 12 h / 25 °C

2: 65 percent / pyridine / diethyl ether / 18 h / 25 °C

3: 80 percent / n-BuNH₂ / tetrahydrofuran / 0.5 h / 25 °C

4: 90 percent / DBU / CH₂Cl₂ / 0.5 h / -30 °C

With pyridine; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-butylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; tert-butyl alcohol; 1: Addition / 2: Acetylation / 3: Deacetylation / 4: Addition;
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q

Reference yield:

: 20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1
3,4,6-tri-O-benzyl-D-glucopyranose

: 250273-52-0
Chloro-acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / pyridine / diethyl ether / 18 h / 25 °C

2: 80 percent / n-BuNH₂ / tetrahydrofuran / 0.5 h / 25 °C

3: 90 percent / DBU / CH₂Cl₂ / 0.5 h / -30 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-butylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Acetylation / 2: Deacetylation / 3: Addition;
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q