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

Base Information

• Chemical Name: (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-(benzyloxy)hexadecanoate
• CAS No.: 134360-68-2
• Molecular Formula: C₄₂H₇₀O₄Si
• Molecular Weight: 667.101
• Mol file: 134360-68-2.mol

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

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

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-(benzyloxy)hexadecanoate

There total 4 articles about (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-(benzyloxy)hexadecanoate 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: 71.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxyhexadecanoate (134453-12-6) → (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-(benzyloxy)hexadecanoate (134360-68-2)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; for 5h; Ambient temperature;

DOI:10.1021/jo00015a027

Reference yield:

benzyl bromide (100-39-0) → (2S,3S,5S)-benzyl 2-hexyl-3-<(tert-butyldimethylsilyl)oxy>-5-(benzyloxy)hexadecanoate (134360-68-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 71 percent / trifluoromethansulfonic acid / CH₂Cl₂; cyclohexane / 5 h / Ambient temperature

With potassium hydroxide; trifluorormethanesulfonic acid; In dichloromethane; cyclohexane;

DOI:10.1021/jo00015a027

Reference yield:

(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-(benzyloxy)hexadecanoate (134360-68-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 71 percent / trifluoromethansulfonic acid / CH₂Cl₂; cyclohexane / 5 h / Ambient temperature

With potassium hydroxide; trifluorormethanesulfonic acid; In dichloromethane; cyclohexane;

DOI:10.1021/jo00015a027

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

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

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

benzyl bromide

Downstream raw materials:

(2S,3S,5S)-benzyl 2-hexyl-3-hydroxy-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