(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

Base Information

Chemical Name:(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol
CAS No.:331414-64-3
Molecular Formula:C₃₀H₄₀O₄
Molecular Weight:464.645
Hs Code.:

Synonyms:(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

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Chemical Property of (4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

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Technology Process of (4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

There total 12 articles about (4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-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: 93.0%

: 331414-51-8
(2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enal

: 1730-25-2
allylmagnesium bromide

: (E)-(4R,5S)-9-Benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

: 331414-64-3
(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

Guidance literature:: allylmagnesium bromide; With (4-^dIcr)2BOMe; In diethyl ether; at 20 ℃; for 1h;

(2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enal; In diethyl ether; at -78 ℃; for 2h;
DOI:10.1021/ja005892h

Reference yield:

: 331414-49-4
(4R)-4-benzyl-3-[(2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enoyl]-oxazolidin-2-one

: 331414-64-3
(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / NaBH₄; H₂O / tetrahydrofuran / 5 - 20 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

3.1: methoxyborane derived from 3-carene / diethyl ether / 1 h / 20 °C

3.2: diethyl ether / 2 h / -78 °C

3.3: aq. NaOH; aq. H₂O₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

With sodium tetrahydroborate; oxalyl dichloride; methoxyborane derived from 3-carene; water; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

: 441018-98-0
trans-4-benzyloxy-1-iodo-2-butene

: 331414-64-3
(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C

1.2: 75 percent / toluene; tetrahydrofuran / 2 h / -45 °C

2.1: 88 percent / NaBH₄; H₂O / tetrahydrofuran / 5 - 20 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

4.1: methoxyborane derived from 3-carene / diethyl ether / 1 h / 20 °C

4.2: diethyl ether / 2 h / -78 °C

4.3: aq. NaOH; aq. H₂O₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

With sodium tetrahydroborate; oxalyl dichloride; methoxyborane derived from 3-carene; water; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00040-6