Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester
• CAS No.: 476371-54-7
• Molecular Formula: C₂₀H₂₂O₄S
• Molecular Weight: 358.458
• Mol file: 476371-54-7.mol

Synonyms:Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester

Chemical Property of Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester

There total 3 articles about Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl 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: 83.0%

(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene (110567-21-0) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester (476371-54-7)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1021/ja0258778

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester (476371-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran; dimethylformamide / 0.25 h / -40 °C

1.2: (+)-IPC₂BH / tetrahydrofuran / 48 h / -10 °C

1.3: 73 percent / aq. H₂O₂; NaOH / 12 h / 20 °C

2.1: 83 percent / pyridine / 12 h / 20 °C

With pyridine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja0258778

Reference yield:

sodium cyclopentadienylide (4984-82-1) → Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester (476371-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran; dimethylformamide / 0.25 h / -40 °C

1.2: (+)-IPC₂BH / tetrahydrofuran / 48 h / -10 °C

1.3: 73 percent / aq. H₂O₂; NaOH / 12 h / 20 °C

2.1: 83 percent / pyridine / 12 h / 20 °C

With pyridine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja0258778

upstream raw materials:

(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

p-toluenesulfonyl chloride

Benzyloxymethyl chloride

sodium cyclopentadienylide

Downstream raw materials:

[2-benzyloxymethyl-5-(tert-butoxycarbonylaminomethyl)cyclopentyl]carbamic acid benzyl ester

(2-benzyloxymethyl-5-cyanocyclopentyl)carbamic acid benzyl ester

[2-(benzyloxymethyl)-5-phenoxycyclopentyl]carbamic acid tert-butyl ester

(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester