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

Base Information

Chemical Name:(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoic acid
CAS No.:474745-89-6
Molecular Formula:C₂₇H₅₀O₆Si₂
Molecular Weight:526.861
Hs Code.:

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

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Chemical Property of (3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoic acid

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Technology Process of (3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoic acid

There total 6 articles about (3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoic 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: 91.0%

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

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

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2,2-dimethyl-2-butene; In tetrahydrofuran; water; at 23 ℃; for 2h;
DOI:10.1021/ol0266875

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2,2-dimethyl-2-butene; 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:

: 474745-94-3
(3S,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoate

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

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

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

With sodium chlorite; sodium dihydrogenphosphate; 2,2-dimethyl-2-butene; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1021/ol0266875