(3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol

Base Information

• Chemical Name: (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol
• CAS No.: 313944-70-6
• Molecular Formula: C₃₆H₄₆O₄Si
• Molecular Weight: 570.844
• Mol file: 313944-70-6.mol

Synonyms:

Chemical Property of (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol

There total 11 articles about (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol 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: 79.0%

((3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-4,6-bis-methoxymethoxy-3a-methyl-octahydro-4,7-ethano-inden-8-ylmethoxy)-tert-butyl-diphenyl-silane (313944-62-6) → (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol (313944-70-6)

Guidance literature:

With bromocatecholborane;

DOI:10.1016/S0040-4039(00)01413-1

Reference yield:

(1S,2R,3S,4S,5R,8S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,8-bis-methoxymethoxy-2-methyl-3-(2-oxo-ethyl)-bicyclo[2.2.2]octane-2-carbaldehyde (313944-59-1) → (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol (313944-70-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

2: 91 percent / Ph₃P; DEAD

3: 99 percent / Super-Hydride

4: 95 percent / NaH

5: 79 percent / B-bromocatecholborane

With samarium diiodide; bromocatecholborane; sodium hydride; lithium triethylborohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Cyclization / 2: Epoxidation / 3: Reduction / 4: Etherification / 5: Substitution;

DOI:10.1016/S0040-4039(00)01413-1

Reference yield:

2-[(1S,2S,3S,4S,6R,7S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-4,7-bis-methoxymethoxy-3-methyl-bicyclo[2.2.2]oct-2-yl]-ethanol (313944-68-2) → (3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol (313944-70-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / PCC

2: 74 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

3: 91 percent / Ph₃P; DEAD

4: 99 percent / Super-Hydride

5: 95 percent / NaH

6: 79 percent / B-bromocatecholborane

With samarium diiodide; bromocatecholborane; sodium hydride; lithium triethylborohydride; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Oxidation / 2: Cyclization / 3: Epoxidation / 4: Reduction / 5: Etherification / 6: Substitution;

DOI:10.1016/S0040-4039(00)01413-1

upstream raw materials:

((3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-4,6-bis-methoxymethoxy-3a-methyl-octahydro-4,7-ethano-inden-8-ylmethoxy)-tert-butyl-diphenyl-silane

benzyl bromide

(1S,2R,3S,4S,5R,8S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,8-bis-methoxymethoxy-2-methyl-3-(2-oxo-ethyl)-bicyclo[2.2.2]octane-2-carbaldehyde

(1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol

Downstream raw materials:

(1R,3aS,4S,7S,7aS,9R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-7a-methyl-octahydro-4,7-ethano-inden-5-one