(1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene

Base Information

• Chemical Name: (1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene
• CAS No.: 351884-92-9
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332

Synonyms:(1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene

Chemical Property of (1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene

There total 2 articles about (1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene 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: 94.0%

chloromethyl methyl ether (107-30-2) + (1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol (243987-96-4) → (1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene (351884-92-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ol015963x

Reference yield:

(1S,5S,7R)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one → (1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene (351884-92-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaBH₄; CeCl₃ / 0 °C

2: 94 percent / Huenig base / CH₂Cl₂

With sodium tetrahydroborate; cerium(III) chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ol015963x

Reference yield: 95.0%

(1R,2S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]oct-3-ene (351884-92-9) → (1S,2S,3R,4S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol (351884-93-0)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water;

DOI:10.1021/ol015963x

upstream raw materials:

chloromethyl methyl ether

(1R,2S,5S,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-3-en-2-ol

Downstream raw materials:

(1S,2S,3R,4S,5S,7R)-7-Benzyloxymethyl-2-methoxymethoxy-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol

(1R,2R,3R,4R)-5-cyclohexene-1,2,3,4-tetrol

(1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene

(1R,2R,3R,4S)-5-cyclohexene-1,2,3,4-tetrol

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