(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

Base Information

Chemical Name:(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid
CAS No.:795308-12-2
Molecular Formula:C₄₁H₅₂O₇Si
Molecular Weight:684.945
Hs Code.:

Synonyms:(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

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Chemical Property of (E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

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Technology Process of (E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

There total 1 articles about (E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid 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%

: 795308-11-1
(2R/S,1'S)-1'-{[(tert-butyldiphenylsilyl)oxy]methyl}-6'-(1,3-dioxolan-2-yl)-4'-methyl-2',4'-hexadien-1'-yl 2-[(4-methoxybenzyl)oxy]-5-hexenoate

: 795308-12-2
(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

Guidance literature:: (2R/S,1'S)-1'-{[(tert-butyldiphenylsilyl)oxy]methyl}-6'-(1",3"-dioxolan-2"-yl)-4'-methyl-2',4'-hexadien-1'-yl 2-[(4-methoxybenzyl)oxy]-5-hexenoate; With potassium hexamethylsilazane; In toluene; at -78 ℃; for 0.75h;

With chloro-trimethyl-silane; In toluene; at 20 ℃; for 3h; Further stages.;
DOI:10.1002/ejoc.200400262

Reference yield:

: 795308-12-2
(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

: (1R,2S,3S,4R)-3-(1',5'-dimethyl-1',4'-hexadien-1'-yl)-4-(hydroxymethyl)-1,2,4-cyclohexanetriol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 94 percent / Grubbs catalyst / toluene; CH₂Cl₂ / 2 h / 40 °C

2.1: 50 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; acetone / 48 h

3.1: 86 percent / DMAP / pyridine / 2 h

4.1: 99 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 20 °C

5.1: lithium aluminum hydride / tetrahydrofuran / 1 h / 0 °C

6.1: 404 mg / camphorsulfonic acid / 2 h

7.1: Cp₂TiCl₂; magnesium turnings; P(OEt)3 / tetrahydrofuran / 0.5 h / 35 °C

7.2: 15 percent / tetrahydrofuran / 1 h / 60 °C

8.1: 71 percent / aq. HCl / tetrahydrofuran / 2 h

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; AD-mix-α; lithium aluminium tetrahydride; methanesulfonamide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; magnesium; triethyl phosphite; Grubbs catalyst first generation; In tetrahydrofuran; pyridine; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 8.1: Takeda's procedure;
DOI:10.1002/ejoc.200400262

Reference yield:

: 795308-12-2
(E)-(2R,3R)-2-But-3-enyl-3-[(E)-3-(tert-butyl-diphenyl-silanyloxy)-propenyl]-6-[1,3]dioxolan-2-yl-2-(4-methoxy-benzyloxy)-4-methyl-hex-4-enoic acid

: 795308-17-7
methyl (1R,2S,3S,4R)-3,4-bis(acetyloxy)-2-[3'-(1,3-dioxolan-2-yl)-1'-methyl-1'-propen-1'-yl]-1-[(4-methoxybenzyl)oxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / Grubbs catalyst / toluene; CH₂Cl₂ / 2 h / 40 °C

2: 50 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; acetone / 48 h

3: 86 percent / DMAP / pyridine / 2 h

With dmap; AD-mix-α; methanesulfonamide; Grubbs catalyst first generation; In pyridine; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1002/ejoc.200400262