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

Base Information

Chemical Name:(2R,4S,5S,8S,10E,12R)-1,5-dibenzyloxy-12-(tert-butyldimethylsilyl)oxymethyl-4-methoxy-2,8,10-trimethyl-10,14-pentadecadien-6-one
CAS No.:135840-28-7
Molecular Formula:C₄₀H₆₂O₅Si
Molecular Weight:651.015
Hs Code.:

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

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Chemical Property of (2R,4S,5S,8S,10E,12R)-1,5-dibenzyloxy-12-(tert-butyldimethylsilyl)oxymethyl-4-methoxy-2,8,10-trimethyl-10,14-pentadecadien-6-one

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Technology Process of (2R,4S,5S,8S,10E,12R)-1,5-dibenzyloxy-12-(tert-butyldimethylsilyl)oxymethyl-4-methoxy-2,8,10-trimethyl-10,14-pentadecadien-6-one

There total 27 articles about (2R,4S,5S,8S,10E,12R)-1,5-dibenzyloxy-12-(tert-butyldimethylsilyl)oxymethyl-4-methoxy-2,8,10-trimethyl-10,14-pentadecadien-6-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: 77.0%

: 186406-67-7
(E)-(2R,4S,5S,8S,12R)-7-Benzenesulfonyl-1,5-bis-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-2,8,10-trimethyl-pentadeca-10,14-dien-6-one

: 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

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;
DOI:10.1016/0040-4039(91)80646-N

Reference yield:

: 186406-55-3
(2S,3S)-4-methyl-2-(2-propenyl)-4-pentene-1,3-diol

: 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

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

2: 90 percent / DCC, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

3: 1.) TBSCl, LDA, HMPA / 1.) THF, -78 deg C, 10 min, 2.) THF, a) RT, 30 min, b) reflux, 2.5 h

4: 86 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

5: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: NaI / acetone / 48 h / Heating

7: dimethylformamide / 15 h / 80 °C

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

9: 74 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) 0 deg C, 2.5 h

10: 77 percent / Bu₃SnH, AIBN / toluene / 5 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0957-4166(96)00445-4

Reference yield:

: 186406-63-3
1-((2S,4S,5S)-5-Allyl-2-phenyl-[1,3]dioxan-4-yl)-ethanol

: 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

Guidance literature:: Multi-step reaction with 13 steps

1: 93 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 40 min

2: 1.) n-BuLi / 1.) THF, hexane, RT, 30 min, 2.) THF, hexane, RT, 6 h

3: 91 percent / aq. AcOH / tetrahydrofuran / 3 h / 60 °C

4: 88 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

5: 90 percent / DCC, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

6: 1.) TBSCl, LDA, HMPA / 1.) THF, -78 deg C, 10 min, 2.) THF, a) RT, 30 min, b) reflux, 2.5 h

7: 86 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

8: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: NaI / acetone / 48 h / Heating

10: dimethylformamide / 15 h / 80 °C

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

12: 74 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) 0 deg C, 2.5 h

13: 77 percent / Bu₃SnH, AIBN / toluene / 5 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tert-butyldimethylsilyl chloride; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0957-4166(96)00445-4