Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 88988-62-9
• Molecular Formula: C₃₂H₃₅ClO₇
• Molecular Weight: 567.079

Synonyms:Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl 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:

allyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (89016-60-4) + Chloroacetic anhydride (541-88-8) → Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (88988-62-9)

Guidance literature:

With pyridine; Yield given;

DOI:10.1016/0008-6215(83)88396-7

Reference yield: 71.2%

Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (88988-62-9) + Chloroacetic anhydride (541-88-8) → Chloro-acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl ester (88988-63-0)

Guidance literature:

With sodium acetate; acetic acid; palladium dichloride; at 60 ℃; for 2h;

DOI:10.1016/0008-6215(83)88396-7

Reference yield:

Chloro-acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (88988-62-9) → Chloro-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-chloro-tetrahydro-pyran-2-ylmethyl ester (88988-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 71.2 percent / PdCl₂, aq. AcOH-AcONa / 2 h / 60 °C

2: 2N⁽¹⁺⁾=CHOSOCl>Cl^(1-) / 1,2-dichloro-ethane

With sodium acetate; <(chlorosulfinyloxy)methylene>dimethylammonium chloride; acetic acid; palladium dichloride; In 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(83)88396-7

upstream raw materials:

allyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chloroacetic anhydride

Downstream raw materials:

Chloro-acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chloro-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-chloro-tetrahydro-pyran-2-ylmethyl ester

allyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Chloro-acetic acid (2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

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