(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol

Base Information

• Chemical Name: (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol
• CAS No.: 137647-81-5
• Molecular Formula: C₂₉H₄₈O₆Si
• Molecular Weight: 520.782

Synonyms:(1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol

Chemical Property of (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol

Chemical Property:

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Technology Process of (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-5-ol

There total 3 articles about (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]decan-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: 73.0%

(1R,3S,4S,5S,6R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4-dimethyl-8-triisopropylsilanyloxymethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-ol (137628-55-8) → (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]decan-5-ol (137647-81-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In dichloromethane; water; for 24h; Ambient temperature;

DOI:10.1021/ja00023a029

Reference yield:

(1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4-dimethyl-8-triisopropylsilanyloxymethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one (137628-54-7) → (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]decan-5-ol (137647-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NaBH₄, CeCl₃ / methanol / 0.08 h

2: 73 percent / m-chloroperbenzoic acid, sodium phosphate / CH₂Cl₂; H₂O / 24 h / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In methanol; dichloromethane; water;

DOI:10.1021/ja00023a029

Reference yield:

(R)-2-[(1R,2S,3S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-6-hydroxy-6-methyl-5-triisopropylsilanyloxymethyl-6H-pyran-3-one → (1R,2R,4R,5S,6S,7S,8S)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-1,7-dimethyl-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.02,4]decan-5-ol (137647-81-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / 48percent aq. HF, 30percent aq. H₂SiF₆ / acetonitrile / 0.33 h / Ambient temperature

2: 99 percent / NaBH₄, CeCl₃ / methanol / 0.08 h

3: 73 percent / m-chloroperbenzoic acid, sodium phosphate / CH₂Cl₂; H₂O / 24 h / Ambient temperature

With sodium tetrahydroborate; fluorosilicic acid; cerium(III) chloride; hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ja00023a029

upstream raw materials:

(1R,3S,4S,5S,6R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4-dimethyl-8-triisopropylsilanyloxymethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-ol

(1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4-dimethyl-8-triisopropylsilanyloxymethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

Downstream raw materials:

(+/-)-tirandamycin B

3-[(2Z,4E)-(S)-1-Hydroxy-6-((1R,2R,4S,6R,7S,8S)-2-hydroxymethyl-1,7-dimethyl-5-oxo-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-4-methyl-hepta-2,4-dien-(E)-ylidene]-pyrrolidine-2,4-dione

1-(2,4-Dimethoxy-benzyl)-3-[(2E,4E)-(S)-6-((1R,2R,4S,6R,7S,8S)-1,7-dimethyl-5-oxo-2-triisopropylsilanyloxymethyl-3,9,10-trioxa-tricyclo[4.3.1.0^2,4]dec-8-yl)-1-hydroxy-4-methyl-hepta-2,4-dien-(Z)-ylidene]-pyrrolidine-2,4-dione

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