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

Base Information

• Chemical Name: (3S,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoate
• CAS No.: 474745-94-3
• Molecular Formula: C₃₁H₅₈O₆Si₂
• Molecular Weight: 582.969
• Mol file: 474745-94-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (3S,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoate 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (5R)-tert-butyl-3,5-dihydroxy-7-[(4-methoxy-benzyl)oxy]-heptanoate → (3S,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoate (474745-94-3) + (3R,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxybenzyl)oxy]-heptanoate

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 23 ℃; for 18h;

DOI:10.1021/ol0266875

Reference yield:

5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester (118207-58-2) → (3S,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoate (474745-94-3)

Guidance literature:

Multi-step reaction with 4 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

With dmap; n-butyllithium; hydrogen; triethylamine; diisopropylamine; tetramethylammonium triacetoxyborohydride; RuCl₂[(R)-BINAP]; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; acetonitrile; 1.1: Noyori hydrogenaion;

DOI:10.1021/ol0266875

Reference yield:

(3R)-methyl-3-hydroxy-5-[(4-methoxybenzyl)oxy]pentanoate (474746-02-6) → (3S,5R)-tert-butyl-3,5-bis(tert-butyldimethylsilanyloxy)-7-[(4-methoxy-benzyl)oxy]-heptanoate (474745-94-3)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 85 percent / tetrahydrofuran; hexane / 1 h / -40 °C

2.1: 86 percent / tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 48 h / -30 °C

3.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 23 °C

With dmap; n-butyllithium; triethylamine; diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/ol0266875

upstream raw materials:

tert-butyldimethylsilyl chloride

5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester

(3R)-methyl-3-hydroxy-5-[(4-methoxybenzyl)oxy]pentanoate

(5R)-tert-butyl-5-hydroxy-7-(4-methoxy-benzyloxy)-3-oxoheptanoate

Downstream raw materials:

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

(2S,4R,4'S,6'R)-1-[6'-benzyloxymethyl-4'-(4-methoxy-benzyloxy)-5',6'-dihydro-4'H-pyran-2'-yl]-6-(4-methoxy-benzyloxy)-hexane-2,4-diol

(2R,4S,2'S,4'R)-2-benzyloxymethyl-6-[2',4'-bis(tert-butyldimethylsilanyloxy)-6'-(4-methoxy-benzyloxy)-hexyl]-4-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran

(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