(3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one

Base Information

• Chemical Name: (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one
• CAS No.: 887142-46-3
• Molecular Formula: C₂₉H₄₆O₄Si
• Molecular Weight: 486.767

Synonyms:(3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one

Chemical Property of (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one

Chemical Property:

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Technology Process of (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one

There total 5 articles about (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-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: 95.0%

(3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-7-hydroxy-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one (887142-46-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 24 ℃; for 0.5h;

DOI:10.1021/ol0602912

Reference yield:

(3aR,5aR,6R,7S,9aS,9bS)-7-Hydroxy-6-hydroxymethyl-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one (887138-29-6) → (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one (887142-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / silver oxide / CH₂Cl₂ / 3 h / 24 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 24 °C

With 2,6-dimethylpyridine; silver(l) oxide; In dichloromethane;

DOI:10.1021/jo062422i

Reference yield:

benzyl bromide (100-39-0) → (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one (887142-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Ag₂O / CH₂Cl₂ / 3 h / 24 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 24 °C

With 2,6-dimethylpyridine; silver(l) oxide; In dichloromethane;

DOI:10.1021/ol0602912

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(3aR,5aR,6R,7S,9aS,9bS)-7-Hydroxy-6-hydroxymethyl-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one

benzyl bromide

(3aR,5aR,6R,7S,9aS,9bS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one

Downstream raw materials:

2-((S)-7-Amino-1,1,3,3-tetramethyl-1,3,9,9a-tetrahydro-2-oxa-fluoren-6-yl)-1-((1S,2R,4aR,5R,6S,8aS)-5-benzyloxymethyl-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-decahydro-naphthalen-1-yl)-ethanone

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