Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester
• CAS No.: 178811-65-9
• Molecular Formula: C₁₆H₂₆O₉S₂
• Molecular Weight: 426.509

Synonyms:Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester

Chemical Property of Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester

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Technology Process of Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester

There total 5 articles about Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-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: 98.0%

methanesulfonyl chloride (124-63-0) + (2S,4S)-5-Benzyloxy-2-methoxymethoxy-pentane-1,4-diol (178811-64-8) → Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester (178811-65-9)

Guidance literature:

With pyridine; In dichloromethane; for 1h;

DOI:10.1080/07328309608005664

Reference yield:

3β-acetoxy-5β-acetoxymethyltetrahydrofuran-2-one (79580-65-7) → Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester (178811-65-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / KCN / methanol

2: 86 percent / NaH / dimethylformamide

3: 97 percent / P₂O₅

4: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h

5: 98 percent / pyridine / CH₂Cl₂ / 1 h

With pyridine; potassium cyanide; lithium aluminium tetrahydride; phosphorus pentoxide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/07328309608005664

Reference yield:

(3S,5S)-5-Benzyloxymethyl-3-hydroxydihydrofuran-2(3H)-one (178811-62-6) → Methanesulfonic acid (1S,3S)-1-benzyloxymethyl-4-methanesulfonyloxy-3-methoxymethoxy-butyl ester (178811-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / P₂O₅

2: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h

3: 98 percent / pyridine / CH₂Cl₂ / 1 h

With pyridine; lithium aluminium tetrahydride; phosphorus pentoxide; In tetrahydrofuran; dichloromethane;

DOI:10.1080/07328309608005664

upstream raw materials:

methanesulfonyl chloride

(2S,4S)-5-Benzyloxy-2-methoxymethoxy-pentane-1,4-diol

3β-acetoxy-5β-acetoxymethyltetrahydrofuran-2-one

(3S,5S)-5-Benzyloxymethyl-3-hydroxydihydrofuran-2(3H)-one

Downstream raw materials:

(2R,4S)-2-Benzyloxymethyl-4-methoxymethoxy-1-oxo-1λ⁵-phospholan-1-ol

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