2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

Base Information

Chemical Name:2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside
CAS No.:686767-31-7
Molecular Formula:C₂₄H₂₆Cl₃NO₆
Molecular Weight:530.833
Hs Code.:

Synonyms:2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

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Chemical Property of 2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

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Technology Process of 2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

There total 6 articles about 2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside 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: 77.0%

: 72657-01-3
1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose

: 545-06-2
trichloroacetonitrile

: 686767-31-7
2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

Guidance literature:: 1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose; In tetrahydrofuran; water; Acidic conditions;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; water;
DOI:10.1021/acschembio.6b00568

Reference yield: 46.0%

: 64-19-7,77671-22-8
acetic acid

: 545-06-2
trichloroacetonitrile

: (3aR,5S,6S,7R,7aR)-6,7-Bis-benzyloxy-2-ethoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

: 686767-31-7
2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

Guidance literature:: acetic acid; (3aR,5S,6S,7R,7aR)-6,7-Bis-benzyloxy-2-ethoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran; In water; at 20 ℃; for 16h;

trichloroacetonitrile; With caesium carbonate; In dichloromethane; at 20 ℃; for 14h;
DOI:10.1021/ja991361l

Reference yield:

: 141554-87-2
3,4-Di-O-Acetyl-β-L-rhamnose 1,2-(ethylorthoacetate)

: 686767-31-7
2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 78 percent / KOH / tetrahydrofuran / 8 h / Heating

2.1: H₂O / 16 h / 20 °C

2.2: 46 percent / Cs₂CO₃ / CH₂Cl₂ / 14 h / 20 °C

With potassium hydroxide; In tetrahydrofuran; water; 1.1: Etherification / 2.1: Esterification / 2.2: trichloroacetimidation;
DOI:10.1021/ja991361l