Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester
• CAS No.: 55287-66-6
• Molecular Formula: C₁₉H₂₃ClO₈
• Molecular Weight: 414.84

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester

There total 2 articles about Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-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:

1,3,4,6-Tetra-O-acetyl-2-O-benzyl-D-galactopyranose (29741-67-1,30253-76-0,53872-77-8,72984-63-5,79733-81-6,80779-87-9,95403-48-8) → Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester (55287-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / TiBr₄ / CH₂Cl₂; ethyl acetate / 48 h / Ambient temperature; further reagent: HBr

2: <(C₂H₅)4N>Cl / acetonitrile / 0.23 h

With tetraethylammonium chloride; titanium(IV) bromide; In dichloromethane; ethyl acetate; acetonitrile;

Reference yield:

→ Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester (55287-66-6)

Guidance literature:

Chlorid 1d, AgClO4, Et4N*Cl;

DOI:10.1016/S0008-6215(00)82362-9

Reference yield: 47.0%

Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester (55287-66-6) + (2,2,2-Trichlorethyl)-2,3-O-isopropyliden-α-L-rhamnopyranosid (70056-61-0) → (2,2,2-Trichlorethyl)-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid (79705-33-2)

Guidance literature:

calcium sulfate; silver perchlorate; silver carbonate; In dichloromethane; at 0 ℃; for 0.5h;

upstream raw materials:

1,3,4,6-Tetra-O-acetyl-2-O-benzyl-D-galactopyranose

Downstream raw materials:

(2,2,2-Trichlorethyl)-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid

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