(1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
• CAS No.: 123060-70-8
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423

Synonyms:(1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Chemical Property of (1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

There total 2 articles about (1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl 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: 53.0%

benzyl bromide (100-39-0) + (1S,2R,3S,4R)-3-Hydroxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (123060-69-5) → (1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (123060-70-8)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(00)82235-2

Reference yield:

(1S,2R,3S,4R)-3-Formyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (116205-36-8) → (1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (123060-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn(BH₄)2 / tetrahydrofuran / 98 h / -78 °C

2: 53 percent / NaH

With zinc(II) tetrahydroborate; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)82235-2

Reference yield: 95.0%

(1S,2R,3S,4R)-3-Benzyloxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (123060-70-8) → (1S,2R,3S,4R,5R)-3-Benzyloxymethyl-5-hydroxy-1-methoxymethoxy-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (123060-71-9)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)82235-2

upstream raw materials:

benzyl bromide

(1S,2R,3S,4R)-3-Hydroxymethyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(1S,2R,3S,4R)-3-Formyl-1-methoxymethoxy-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Downstream raw materials:

(1S,2R,3S,4R,5R)-3-Benzyloxymethyl-5-hydroxy-1-methoxymethoxy-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(1S,5R,6S,7R,8R)-6-Benzyloxymethyl-2-oxa-tricyclo[5.2.2.0^1,5]undecane-3,8-diol

C₂₀H₂₄O₄

C₂₀H₂₂O₄

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