(2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 89731-60-2
• Molecular Formula: C₁₂H₁₅ClO₆
• Molecular Weight: 290.701

Synonyms:(2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 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: 80.0%

Acetic acid (3aS,4S,6R,7R,7aS)-6-acetoxymethyl-4-(4-chloro-phenoxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (120489-21-6) → (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (89731-60-2)

Guidance literature:

With Dowex-1 (basic) resin; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(88)84013-8

Reference yield:

4,6-di-O-acetyl-2,3-O-carbonyl-α-D-mannopyranosyl bromide (53958-21-7) → (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (89731-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / dicyclohexyl-18-crown-6 / acetonitrile / Ambient temperature

2: 80 percent / Dowex-1 (basic) resin / methanol / Ambient temperature

With Dowex-1 (basic) resin; perhydrodibenzo-18-crown-6; In methanol; acetonitrile;

DOI:10.1016/0008-6215(88)84013-8

Reference yield:

potassium 4-chlorophenoxide (1121-74-0) → (2S,3S,4S,5S,6R)-2-(4-Chloro-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (89731-60-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / dicyclohexyl-18-crown-6 / acetonitrile / Ambient temperature

2: 80 percent / Dowex-1 (basic) resin / methanol / Ambient temperature

With Dowex-1 (basic) resin; perhydrodibenzo-18-crown-6; In methanol; acetonitrile;

DOI:10.1016/0008-6215(88)84013-8

upstream raw materials:

Acetic acid (3aS,4S,6R,7R,7aS)-6-acetoxymethyl-4-(4-chloro-phenoxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

4,6-di-O-acetyl-2,3-O-carbonyl-α-D-mannopyranosyl bromide

potassium 4-chlorophenoxide

Downstream raw materials:

p-chlorophenyl 2-O-β-D-mannopyranosyl-β-D-mannopyranoside

p-chlorophenyl 6-O-β-D-mannopyranosyl-β-D-mannopyranoside

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