(2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate

Base Information

• Chemical Name: (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate
• CAS No.: 134453-12-6
• Molecular Formula: C₃₅H₆₄O₄Si
• Molecular Weight: 576.976
• Mol file: 134453-12-6.mol

Synonyms:(2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate

Chemical Property of (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate

There total 3 articles about (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate (134453-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / N,N-diisopropylethylamine / dimethylformamide / 48 h

2: 1) aq. KOH / 1) dioxane, 80 min, 2) THF, hexamethylphosphorus triamide, 16 h, RT

With potassium hydroxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo00015a027

Reference yield:

benzyl bromide (100-39-0) + (3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one (134360-67-1) → (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate (134453-12-6)

Guidance literature:

With potassium hydroxide; Yield given. Multistep reaction; 1) dioxane, 80 min, 2) THF, hexamethylphosphorus triamide, 16 h, RT;

DOI:10.1021/jo00015a027

Reference yield:

(3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one (68711-33-1) → (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate (134453-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / N,N-diisopropylethylamine / dimethylformamide / 48 h

2: 1) aq. KOH / 1) dioxane, 80 min, 2) THF, hexamethylphosphorus triamide, 16 h, RT

With potassium hydroxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo00015a027

upstream raw materials:

benzyl bromide

(3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one

(3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-(benzyloxy)hexadecanoate

(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

(2S,3S,5S)-5-(benzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

(3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one