(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester
CAS No.:195377-39-0
Molecular Formula:C₃₆H₅₀O₈Si
Molecular Weight:638.874
Hs Code.:

Synonyms:(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

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Chemical Property of (2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

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Technology Process of (2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

There total 9 articles about (2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl 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: 92.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 235791-67-0
(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester

: 195377-39-0
(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

Guidance literature:: With 1H-imidazole; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)00782-0

Reference yield: 80.0%

: 195377-38-9
(3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

: 195377-39-0
(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

Guidance literature:: (3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

With Davis oxaziridine reagent; In tetrahydrofuran; toluene; at -78 ℃; for 3h;
DOI:10.1021/ja970251g

Reference yield:

: 139190-51-5
Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

: 195377-39-0
(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C

1.2: 92 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: 91 percent / Davis oxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

3.1: 92 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 48 h / 0 - 20 °C

4.1: 97 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 - 0 °C

5.1: oxalyl chloride; DMSO; triethylamin / CH₂Cl₂ / 0.83 h / -55 - -30 °C

6.1: 8.5 g / CH₂Cl₂ / 14 h / 20 °C

7.1: CuI / tetrahydrofuran; diethyl ether / 0.5 h / -15 - 0 °C

7.2: 85 percent / Me₃SiCl / tetrahydrofuran; diethyl ether / 3 h / -78 °C

8.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

8.2: 80 percent / Davis oxaziridine reagent / tetrahydrofuran; toluene / 3 h / -78 °C

With dmap; copper(l) iodide; oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: complexation / 1.2: Addition / 2.1: Metallation / 2.2: Oxidation / 3.1: Etherification / 4.1: Reduction / 5.1: Swern oxidation / 6.1: Wittig reaction / 7.1: complexation / 7.2: Addition / 8.1: Metallation / 8.2: Oxidation;
DOI:10.1021/ja970251g