((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester

Base Information

• Chemical Name: ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester
• CAS No.: 137548-48-2
• Molecular Formula: C₃₈H₇₁O₅PSi₂
• Molecular Weight: 695.123

Synonyms:

Chemical Property of ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester

Chemical Property:

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Useful:

Technology Process of ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester

There total 4 articles about ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester 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: 83.0%

[(R)-4-((1R,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-yl)-pentyl]-phosphonic acid dimethyl ester (137577-52-7) + [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1) → ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester (137548-48-2)

Guidance literature:

With n-butyllithium;

DOI:10.1016/S0040-4039(00)92270-6

Reference yield:

tert-Butyl-[(1R,3aR,4S,7aR)-1-((R)-4-iodo-1-methyl-butyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane (122778-18-1) → ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester (137548-48-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 26 percent / Heating

2: 98 percent / AG-50W-X₄ cationic exchange resin / methanol

3: 86 percent / Swern-oxidation

4: 83 percent / BuLi

With n-butyllithium; AG-50W-X₄ cationic exchange resin; In methanol;

DOI:10.1016/S0040-4039(00)92270-6

Reference yield:

{(R)-4-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-pentyl}-phosphonic acid dimethyl ester → ((R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentyl)-phosphonic acid dimethyl ester (137548-48-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / AG-50W-X₄ cationic exchange resin / methanol

2: 86 percent / Swern-oxidation

3: 83 percent / BuLi

With n-butyllithium; AG-50W-X₄ cationic exchange resin; In methanol;

DOI:10.1016/S0040-4039(00)92270-6

upstream raw materials:

[(R)-4-((1R,3aR,7aR)-7a-Methyl-4-oxo-octahydro-inden-1-yl)-pentyl]-phosphonic acid dimethyl ester

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

tert-Butyl-[(1R,3aR,4S,7aR)-1-((R)-4-iodo-1-methyl-butyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane

[(R)-4-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-pentyl]-phosphonic acid dimethyl ester

Downstream raw materials:

1α-hydroxy-25-oxa-25-phospha-26,27-dioxa-26,27-dimethylvitamin D₃

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