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

Base Information

Chemical Name:(2S,3R,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-2-methoxymethoxy-3-methylpentanoic acid methyl ester
CAS No.:195377-36-7
Molecular Formula:C₃₃H₄₄O₇Si
Molecular Weight:580.794
Hs Code.:

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

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

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

There total 3 articles about (2S,3R,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-2-methoxymethoxy-3-methylpentanoic 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%

: 107-30-2
chloromethyl methyl ether

: 183119-33-7
(2S,3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-2-hydroxy-3-methylpentanoic acid methyl ester

: 195377-36-7
(2S,3R,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-2-methoxymethoxy-3-methylpentanoic acid methyl ester

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 48h;
DOI:10.1021/ja970251g

Reference yield:

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

: 195377-36-7
(2S,3R,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-2-methoxymethoxy-3-methylpentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 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

With dmap; copper(l) iodide; potassium hexamethylsilazane; 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;
DOI:10.1021/ja970251g

Reference yield:

: 139190-55-9
(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

: 195377-36-7
(2S,3R,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-2-methoxymethoxy-3-methylpentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 91 percent / Davis oxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

2.1: 92 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 48 h / 0 - 20 °C

With dmap; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Metallation / 1.2: Oxidation / 2.1: Etherification;
DOI:10.1021/ja970251g