Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester
• CAS No.: 133346-38-0
• Molecular Formula: C₃₃H₄₁NO₆
• Molecular Weight: 547.692

Synonyms:Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester

Chemical Property of Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester

There total 2 articles about Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl 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:

(3aS)-4t,5c,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole (73174-60-4) → Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester (133346-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn dust, aq. 85percent AcOH / 1 h / 50 - 55 °C

2: tetrahydrofuran / 50 °C

With acetic acid; zinc; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)97253-8

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + ((1S,2R,3S,4R,5S)-2,3,4-Tris-benzyloxy-5-methylamino-cyclopentyl)-methanol (138506-39-5) → Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester (133346-38-0)

Guidance literature:

In tetrahydrofuran; at 50 ℃; Yield given;

DOI:10.1016/S0040-4039(00)97253-8

Reference yield: 100.0%

Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester (133346-38-0) → Methyl-((1S,2R,3S,4R,5R)-2,3,4-tris-benzyloxy-5-formyl-cyclopentyl)-carbamic acid tert-butyl ester (133346-39-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.5h;

DOI:10.1016/S0040-4039(00)97253-8

upstream raw materials:

di-tert-butyl dicarbonate

((1S,2R,3S,4R,5S)-2,3,4-Tris-benzyloxy-5-methylamino-cyclopentyl)-methanol

(3aS)-4t,5c,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole

Downstream raw materials:

((1S,4S,5R)-4,5-Bis-benzyloxy-2-formyl-cyclopent-2-enyl)-methyl-carbamic acid tert-butyl ester

Methyl-((1S,2R,3S,4R,5S)-2,3,4-tris-benzyloxy-5-formyl-cyclopentyl)-carbamic acid tert-butyl ester

Methyl-((1S,2R,3S,4R,5R)-2,3,4-tris-benzyloxy-5-formyl-cyclopentyl)-carbamic acid tert-butyl ester

Methyl-((1S,2R,3S,4R,5R)-2,3,4-tris-benzyloxy-5-hydroxymethyl-cyclopentyl)-carbamic acid tert-butyl ester

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