(1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one

Base Information

• Chemical Name: (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one
• CAS No.: 116287-78-6
• Molecular Formula: C₂₄H₂₂O₆
• Molecular Weight: 406.435

Synonyms:(1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one

Chemical Property of (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one

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Technology Process of (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one

There total 3 articles about (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one 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: 71.0%

C27H24O9 → (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-dien-8-one (116287-78-6)

Guidance literature:

With sodium tetrahydroborate; samarium (III) iodide; In tetrahydrofuran; at 0 ℃; 1.) 0 deg C, 2.) 5-15 deg C;

DOI:10.1016/S0040-4039(00)96841-2

Reference yield:

(1R,2S,6S,7S)-5,6-Bis-benzyloxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-diene-10-carboxylic acid (116287-77-5) → (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-dien-8-one (116287-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: EtN₃ / tetrahydrofuran / 0 °C

2: 71 percent / 1.) SmI₃, 2.) NaBH₄ / tetrahydrofuran / 0 °C / 1.) 0 deg C, 2.) 5-15 deg C

With sodium tetrahydroborate; samarium (III) iodide; ethyl azide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96841-2

Reference yield:

(1S,2S,6S,7R)-5,6-Bis-benzyloxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-diene-10-carboxylic acid 2-trimethylsilanyl-ethyl ester (104319-20-2) → (1R,2S,6S,7S)-5,6-Bis-benzyloxy-10-hydroxymethyl-3,9-dioxa-tricyclo[5.2.2.02,6]undeca-4,10-dien-8-one (116287-78-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / F^(1-)

2: EtN₃ / tetrahydrofuran / 0 °C

3: 71 percent / 1.) SmI₃, 2.) NaBH₄ / tetrahydrofuran / 0 °C / 1.) 0 deg C, 2.) 5-15 deg C

With sodium tetrahydroborate; samarium (III) iodide; fluoride; ethyl azide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96841-2

upstream raw materials:

(1R,2S,6S,7S)-5,6-Bis-benzyloxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-diene-10-carboxylic acid

(1S,2S,6S,7R)-5,6-Bis-benzyloxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-diene-10-carboxylic acid 2-trimethylsilanyl-ethyl ester

Downstream raw materials:

(2S,6S)-5,6-Bis-benzyloxy-10-methyl-3,9-dioxa-tricyclo[5.2.2.0^2,6]undeca-4,10-dien-8-one

(3aS,4S,7aR)-3,3a-Bis-benzyloxy-6-methyl-7-oxo-3a,4,7,7a-tetrahydro-benzofuran-4-carboxylic acid methyl ester

(3aS,7R,7aS)-3a-Benzyloxy-7-hydroxy-6-methyl-3-oxo-2,3,3a,4,7,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester

(3aS,4S,7S,7aS)-3a-Benzyloxy-7-hydroxy-6-methyl-3-oxo-2,3,3a,4,7,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester

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