Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester
• CAS No.: 914402-49-6
• Molecular Formula: C₁₈H₂₆O₆S
• Molecular Weight: 370.467

Synonyms:Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester

Chemical Property of Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester

There total 2 articles about Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-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:

(2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde (104322-68-1) → Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester (914402-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Zn; NH₄Cl / H₂O; tetrahydrofuran / 0 °C

2: TEA / CH₂Cl₂

With TEA; ammonium chloride; zinc; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tetlet.2006.08.026

Reference yield:

(R)-1-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (S)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester + Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester (914402-49-6)

Guidance literature:

With TEA; In dichloromethane;

DOI:10.1016/j.tetlet.2006.08.026

Reference yield: 85.0%

Methanesulfonic acid (R)-1-[(S)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl ester (914402-49-6) → (S)-4-((1R,2S)-2-Azido-1-benzyloxy-pent-4-enyl)-2,2-dimethyl-[1,3]dioxolane (914402-56-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1016/j.tetlet.2006.08.026

upstream raw materials:

methanesulfonyl chloride

(2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

Downstream raw materials:

(S)-4-((1R,2S)-2-Azido-1-benzyloxy-pent-4-enyl)-2,2-dimethyl-[1,3]dioxolane

{(S)-1-[(R)-Benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-enyl}-carbamic acid tert-butyl ester

[(1S,2R,3S)-1-(3-Azido-propyl)-2-benzyloxy-3,4-dihydroxy-butyl]-carbamic acid tert-butyl ester

{(S)-1-[(R)-Benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-4-hydroxy-butyl}-carbamic acid tert-butyl ester

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