(E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

Base Information

Chemical Name:(E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol
CAS No.:186406-68-8
Molecular Formula:C₄₀H₆₄O₅Si
Molecular Weight:653.031
Hs Code.:

Synonyms:(E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

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Chemical Property of (E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

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Technology Process of (E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

There total 26 articles about (E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-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: 92.0%

: 135840-28-7
(2R,4S,5S,8S,10E,12R)-1,5-dibenzyloxy-12-(tert-butyldimethylsilyl)oxymethyl-4-methoxy-2,8,10-trimethyl-10,14-pentadecadien-6-one

: 186406-68-8
(E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -78 ℃; for 0.5h;
DOI:10.1016/S0957-4166(96)00445-4

Reference yield:

: 17618-04-1
2,5-di-O-benzyl-D-mannitol

: 186406-68-8
(E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 100 percent / Pb(OAc)4 / benzene / 8 h / Ambient temperature

3: 78 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -78 °C

4: 1.) KH / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 3 h

5: 1.) thexylborane, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, -15 deg C, 2 h, 2.) THF, RT, 30 min

6: 1.) KH / 1.) THF, -15 deg C, 15 min, 2.) THF, RT, 2 h

7: 92 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

8: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) 0 deg C, 30 min

9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 2.5 h

10: 74 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) 0 deg C, 2.5 h

11: 77 percent / Bu₃SnH, AIBN / toluene / 5 h / Heating

12: 92 percent / LiAlH₄ / diethyl ether / 0.5 h / -78 °C

With 1H-imidazole; lead(IV) acetate; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); thexylborane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0957-4166(96)00445-4

Reference yield:

: 100-39-0
benzyl bromide

: 186406-68-8
(E)-(2R,4S,5R,6R,8S,12R)-1,5-Bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) KH / 1.) THF, -15 deg C, 15 min, 2.) THF, RT, 2 h

2: 92 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) 0 deg C, 30 min

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 2.5 h

5: 74 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) 0 deg C, 2.5 h

6: 77 percent / Bu₃SnH, AIBN / toluene / 5 h / Heating

7: 92 percent / LiAlH₄ / diethyl ether / 0.5 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0957-4166(96)00445-4