(3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide

Base Information

• Chemical Name: (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide
• CAS No.: 172293-74-2
• Molecular Formula: C₂₄H₄₆BrNO₆Si₃
• Molecular Weight: 608.793

Synonyms:(3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide

Chemical Property of (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide

Chemical Property:

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Technology Process of (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide

There total 3 articles about (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide 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:

(S)-3-[(2S,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-hydroxy-propionic acid tert-butyl ester (141277-17-0) → (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide (172293-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Zn, (CH₃)3SiCl / CH₂Cl₂ / 0.03 h / Ambient temperature

2: AlMe₃ / Ambient temperature; 1.) 30 min, 2.) 12 h

3: HMDS, pyridine / 3 h / Ambient temperature

With pyridine; chloro-trimethyl-silane; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; In dichloromethane;

DOI:10.1021/jo00127a047

Reference yield:

(4S,5R,1'S)-5-<2'-<(4-Bromobenzyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane (172293-72-0) → (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide (172293-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: AlMe₃ / Ambient temperature; 1.) 30 min, 2.) 12 h

2: HMDS, pyridine / 3 h / Ambient temperature

With pyridine; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane;

DOI:10.1021/jo00127a047

Reference yield:

chloro-trimethyl-silane (75-77-4) + (3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide (1053643-71-2) → (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide (172293-74-2)

Guidance literature:

With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; for 3h; Yield given; Ambient temperature;

DOI:10.1021/jo00127a047

upstream raw materials:

chloro-trimethyl-silane

(3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide

(S)-3-[(2S,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-hydroxy-propionic acid tert-butyl ester

(4S,5R,1'S)-5-<2'-<(4-Bromobenzyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane

Downstream raw materials:

(3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(1,3-dithia-2-cyclohexyl)-1-hexanone

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