(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

Base Information

Chemical Name:(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester
CAS No.:474745-88-5
Molecular Formula:C₄₉H₇₆O₉Si₂
Molecular Weight:865.308
Hs Code.:

(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

Synonyms:(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

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Chemical Property of (3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

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Technology Process of (3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

There total 12 articles about (3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl 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: 98.0%

: 474745-90-9
(2R,4S)-(Z)-1-benzyloxy-4-(4-methoxy-benzyloxy)-hept-5-en-2-ol

: 474745-89-6
(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoic acid

: 474745-88-5
(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

Guidance literature:: (3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In dichloromethane; at 23 ℃; for 3h;

(2R,4S)-(Z)-1-benzyloxy-4-(4-methoxy-benzyloxy)-hept-5-en-2-ol; With dmap; In dichloromethane; at 23 ℃; for 4h; Further stages.;
DOI:10.1021/ol0266875

Reference yield:

: 118207-58-2
5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester

: 474745-88-5
(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: H₂ / (R)-BINAP-Ru(II)Cl₂ / methanol / 72 h / 23 °C / 76005.1 Torr

2.1: nBuLi; diisopropylamine / tetrahydrofuran; hexane / 1 h / -40 °C

2.2: 85 percent / tetrahydrofuran; hexane / 1 h / -40 °C

3.1: 86 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 48 h / -30 °C

4.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 23 °C

5.1: 94 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

6.1: 91 percent / 2,2-dimethyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; tetrahydrofuran / 2 h / 23 °C

7.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / CH₂Cl₂ / 3 h / 23 °C

7.2: 98 percent / DMAP / CH₂Cl₂ / 4 h / 23 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2,2-dimethyl-2-butene; 2,4,6-trichlorobenzoyl chloride; hydrogen; diisobutylaluminium hydride; triethylamine; diisopropylamine; tetramethylammonium triacetoxyborohydride; RuCl₂[(R)-BINAP]; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetic acid; acetonitrile; 1.1: Noyori hydrogenaion;
DOI:10.1021/ol0266875

Reference yield:

: (4'R)-(Z)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-pent-3-en-2-ol

: 474745-88-5
(3S,5R,1'R,3'S)-3,5-bis(tert-butyldimethylsilanyloxy)-7-(4-methoxy-benzyloxy)-heptanoic acid (Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: KHMDS; Et₃N / tetrahydrofuran; toluene / 1 h / -78 °C

1.2: 99 percent / tetrahydrofuran; toluene / 1 h / 23 °C

2.1: 90 percent / AcOH / H₂O; tetrahydrofuran / 48 h / 23 °C

3.1: dibutyltin oxide / 2 h / Heating

3.2: 83 percent / CsF; tetrabutylammonium iodide / dimethylformamide / 12 h

4.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / CH₂Cl₂ / 3 h / 23 °C

4.2: 98 percent / DMAP / CH₂Cl₂ / 4 h / 23 °C

With 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; di(n-butyl)tin oxide; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/ol0266875