Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester
• CAS No.: 146176-82-1
• Molecular Formula: C₃₆H₃₈O₈S
• Molecular Weight: 630.759

Synonyms:Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester

Chemical Property of Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester

There total 3 articles about Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl 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: 75.0%

Toluene-4-sulfonic acid (3aR,5R,6S,7R,8S)-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-yl ester (146176-86-5) → Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester (146176-82-1)

Guidance literature:

With hydrogen; boric acid; nickel; In methanol; water;

DOI:10.1016/S0040-4039(00)74717-4

Reference yield:

(3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-ol (141077-21-6,141195-15-5) → Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester (146176-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / pyridine / 20 °C

2: 75 percent / hydrogen, B(OH)3 / Ra/Ni / methanol; H₂O

With pyridine; hydrogen; boric acid; nickel; In methanol; water;

DOI:10.1016/S0040-4039(00)74717-4

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (1R,2S,3S,4R,6S)-2,3,4-tris-benzyloxy-6-hydroxymethyl-5-oxo-cycloheptyl ester (146176-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / pyridine / 20 °C

2: 75 percent / hydrogen, B(OH)3 / Ra/Ni / methanol; H₂O

With pyridine; hydrogen; boric acid; nickel; In methanol; water;

DOI:10.1016/S0040-4039(00)74717-4

upstream raw materials:

Toluene-4-sulfonic acid (3aR,5R,6S,7R,8S)-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-yl ester

(3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-ol

p-toluenesulfonyl chloride

Downstream raw materials:

Toluene-4-sulfonic acid (1R,2S,3S,4R)-2,3,4-tris-benzyloxy-6-chloro-5-oxo-cycloheptyl ester

(2R,3S,4R,5S) 5-azido-2,3,4-tris(benzyloxy) cycloheptane-1-one

(1S,2R,3S,4S,5S) 1-azido-5-hydroxy-2,3,4-tris(benzyloxy) cycloheptane

Toluene-4-sulfonic acid (1R,2S,3S,4R)-2,3,4-tris-benzyloxy-5-oxo-cycloheptyl ester

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