(1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol

Base Information

• Chemical Name: (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol
• CAS No.: 281678-81-7
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278

Synonyms:(1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol

Chemical Property of (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol

There total 2 articles about (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-ol 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:

(1R,2R,4S,6R,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-one (180519-84-0) → (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-ol (281678-81-7)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃;

DOI:10.1016/S0040-4039(00)00216-1

Reference yield:

(1R,5R,7S)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one → (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-ol (281678-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O₂; NaOH / tetrahydrofuran / 0 °C

2: NaBH₄; CeCl₃*7H₂O / methanol / 0 °C

With sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; dihydrogen peroxide; In tetrahydrofuran; methanol; 1: Epoxidation / 2: Reduction;

DOI:10.1016/S0040-4039(00)00216-1

Reference yield: 96.0%

benzoyl chloride (98-88-4) + (1R,2R,4R,5R,6S,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]nonan-5-ol (281678-81-7) → Benzoic acid (1R,2R,4R,5R,6R,7S)-7-benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.02,4]non-5-yl ester (281678-82-8)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1016/S0040-4039(00)00216-1

upstream raw materials:

(1R,2R,4S,6R,7S)-7-Benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one

Downstream raw materials:

Benzoic acid (1R,2R,4R,5R,6R,7S)-7-benzyloxymethyl-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]non-5-yl ester

(1R,2S,6R,7R,8R,10S)-10-Benzyloxymethyl-4,4-dimethyl-3,5,9,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecan-7-ol

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