Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester
• CAS No.: 147127-70-6
• Molecular Formula: C₁₈H₂₀O₅S
• Molecular Weight: 348.42
• Mol file: 147127-70-6.mol

Synonyms:Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester

There total 3 articles about Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl 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: 71.0%

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol (78469-85-9,78513-07-2,78513-15-2,84621-89-6,87172-27-8,95672-91-6,98048-62-5,98048-63-6,78513-12-9) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester (147127-70-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -10 ℃;

DOI:10.1021/jo00055a029

Reference yield:

<2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranemethanol (78513-15-2) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester (147127-70-6) + Toluene-4-sulfonic acid (2R,3R)-3-benzyloxymethyl-oxiranylmethyl ester (200205-69-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -10 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00055a029

Reference yield:

(E)-4-(benzyloxy)-2-buten-1-ol (80885-30-9,81028-03-7,69152-88-1) → Toluene-4-sulfonic acid (2S,3S)-3-benzyloxymethyl-oxiranylmethyl ester (147127-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / (+)-DIPT, Ti(OiPr)4, t-BuOOH, molecular sieves 4 Angstroem / CH₂Cl₂ / -34 °C

2: 71 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / -10 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; L-(+)-diisopropyl tartrate; 4 A molecular sieve; triethylamine; In dichloromethane;

DOI:10.1021/jo00055a029

upstream raw materials:

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol

p-toluenesulfonyl chloride

<2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranemethanol

(E)-4-(benzyloxy)-2-buten-1-ol

Downstream raw materials:

(S)-1-(benzyloxy)but-3-en-2-ol

(2R)-1-(benzyloxy)but-3-en-2-ol