(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

Base Information

Chemical Name:(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester
CAS No.:826994-99-4
Molecular Formula:C₃₇H₅₆O₉
Molecular Weight:644.846
Hs Code.:

(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

Synonyms:(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

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Chemical Property of (E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

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Technology Process of (E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

There total 18 articles about (E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl 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: 74.0%

: 38050-71-4
9-methoxy-9-BBN

: 826994-91-6
(2R,4R,5S)-5-(2-iodoethyl)-4-[(4-methoxybenzyl)oxy]-2-methyl-2-propyltetrahydrofuran

: 826994-98-3
(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-4-iodo-2-methyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-pent-3-enyl] ester 1-methyl ester

: 826994-99-4
(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

Guidance literature:: (2R,4R,5S)-5-(2-iodoethyl)-4-[(4-methoxybenzyl)oxy]-2-methyl-2-propyltetrahydrofuran; With tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 ℃; for 0.0833333h;

9-methoxy-9-BBN; In tetrahydrofuran; diethyl ether; pentane; at -78 - 20 ℃; for 1.25h;

(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-4-iodo-2-methyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-pent-3-enyl] ester 1-methyl ester; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; triphenyl-arsane; In various solvents; at 20 ℃; for 2h;
DOI:10.1021/ja044130+

Reference yield:

: 18871-63-1
3,3-ethylenedioxybutanal

: 826994-99-4
(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Pd(OAc)2; ZnEt₂; PPh₃ / tetrahydrofuran; hexane / 16 h / -78 - -20 °C

2.1: NaH / dimethylformamide / 1 h / 0 °C

2.2: 94 percent / tetrabutylammonium iodide / dimethylformamide / 17 h / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran / 1.5 h / -78 - -20 °C

3.2: 95 percent / tetrahydrofuran / 16 h / -78 - 5 °C

4.1: Cp₂ZrHCl / benzene / 4 h / 50 °C

4.2: 61 percent / I₂ / benzene; CH₂Cl₂ / -15 °C

5.1: 89 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 2 h / 20 °C / pH 7

6.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h / 20 °C

6.2: 200 mg / DMAP / toluene / 1 h

7.1: t-BuLi / tetrahydrofuran; diethyl ether; pentane / 0.08 h / -78 °C

7.2: tetrahydrofuran; diethyl ether; pentane / 1.25 h / -78 - 20 °C

7.3: 74 percent / [PdCl₂(dppf)]; K₃PO₄; Ph₃As / various solvents / 2 h / 20 °C

With palladium diacetate; Schwartz's reagent; phosphate buffer; 2,4,6-trichlorobenzoyl chloride; tert.-butyl lithium; diethylzinc; sodium hydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.2: Yamaguchi esterification;
DOI:10.1021/ja044130+

Reference yield:

: 370578-60-2
(2S)-methyl-4-(triisopropyl-silanyloxy)-butyraldehyde

: 826994-99-4
(E)-(S)-4-Methyl-hex-2-enedioic acid 6-[(E)-(1S,2R)-6-[(2S,3R,5R)-3-(4-methoxy-benzyloxy)-5-methyl-5-propyl-tetrahydro-furan-2-yl]-2,4-dimethyl-1-(2-methyl-[1,3]dioxolan-2-ylmethyl)-hex-3-enyl] ester 1-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / DBU; LiCl / acetonitrile / 16 h / 20 °C

2.1: 100 percent / HF*pyridine / acetonitrile / 1.5 h / 20 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 20 °C

4.1: NaClO₂; NaH₂PO₄; 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O / 2 h

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h / 20 °C

5.2: 200 mg / DMAP / toluene / 1 h

6.1: t-BuLi / tetrahydrofuran; diethyl ether; pentane / 0.08 h / -78 °C

6.2: tetrahydrofuran; diethyl ether; pentane / 1.25 h / -78 - 20 °C

6.3: 74 percent / [PdCl₂(dppf)]; K₃PO₄; Ph₃As / various solvents / 2 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; tert.-butyl lithium; pyridine hydrogenfluoride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; pentane; 3.1: Swern oxidation / 5.2: Yamaguchi esterification;
DOI:10.1021/ja044130+