(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

Base Information

Chemical Name:(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene
CAS No.:474745-87-4
Molecular Formula:C₅₀H₇₈O₈Si₂
Molecular Weight:863.336
Hs Code.:

(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

Synonyms:(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

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Chemical Property of (3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

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Technology Process of (3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

There total 14 articles about (3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene 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: 75.0%

: 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

: 474745-87-4
(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

Guidance literature:: With pyridine; In tetrahydrofuran; toluene; at 0 - 23 ℃;
DOI:10.1021/ol0266875

Reference yield:

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

: 474745-87-4
(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

Guidance literature:: Multi-step reaction with 8 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

8.1: 75 percent / pyridine / tetrahydrofuran; toluene / 0 - 23 °C

With pyridine; 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; toluene; acetonitrile; 1.1: Noyori hydrogenaion / 8.1: Tebbe olefination;
DOI:10.1021/ol0266875

Reference yield:

: (3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanal

: 474745-87-4
(3R,5S,1'R,3'S)-1-[3,5-bis(tert-butyldimethylsilanyloxy)-7-((Z)-1'-benzyloxymethyl-3'-(4-methoxy-benzyloxy)-hex-4'-enyloxy)-oct-7-enyloxymethyl]-4-methoxybenzene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 91 percent / 2,2-dimethyl-2-butene; NaH₂PO₄; NaClO₂ / H₂O; tetrahydrofuran / 2 h / 23 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / CH₂Cl₂ / 3 h / 23 °C

2.2: 98 percent / DMAP / CH₂Cl₂ / 4 h / 23 °C

3.1: 75 percent / pyridine / tetrahydrofuran; toluene / 0 - 23 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2,2-dimethyl-2-butene; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 3.1: Tebbe olefination;
DOI:10.1021/ol0266875