N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide
• CAS No.: 1388155-12-1
• Molecular Formula: C₃₅H₆₇NO₄SSi
• Molecular Weight: 626.073

Synonyms:N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide

Chemical Property of N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide

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Technology Process of N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide

There total 4 articles about N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide 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: 68.0%

(S)-N-(2-(benzyloxy)ethylidene)-2-methylpropane-2-sulfinamide (944814-28-2) + (R)-2-((tert-butyldimethylsilyl)oxy)hexadecanal (1388155-11-0) → N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide (1388155-12-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; tert-butyl alcohol; at -78 ℃; for 5h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2012.05.120

Reference yield:

C12H24O4Si (1244958-79-9) → N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide (1388155-12-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

1.2: 6 h / -78 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C

3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere

3.2: 4 h / 20 °C / Saturated solution

4.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere

With n-butyllithium; samarium diiodide; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; In tetrahydrofuran; methanol; toluene; tert-butyl alcohol; 1.1: Wittig reaction / 1.2: Wittig reaction;

DOI:10.1016/j.tet.2012.05.120

Reference yield:

n-undecyltriphenylphosphonium bromide (60669-22-9) → N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide (1388155-12-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

1.2: 6 h / -78 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C

3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere

3.2: 4 h / 20 °C / Saturated solution

4.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere

With n-butyllithium; samarium diiodide; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; In tetrahydrofuran; methanol; toluene; tert-butyl alcohol; 1.1: Wittig reaction / 1.2: Wittig reaction;

DOI:10.1016/j.tet.2012.05.120

upstream raw materials:

(S)-N-(2-(benzyloxy)ethylidene)-2-methylpropane-2-sulfinamide

(R)-2-((tert-butyldimethylsilyl)oxy)hexadecanal

C₁₂H₂₄O₄Si

(R)-methyl 2-(tert-butyldimethylsilyloxy)hexadec-5-enoate

Downstream raw materials:

C₂₅H₄₅NO₃*ClH

tert-butyl (2S,3S,4R)-1-(benzyloxy)-3,4-dihydroxyoctadecan-2-ylcarbamate

(2S,3S,4R)-1-(benzyloxy)-3,4-bis(tert-butyldimethylsilyloxy)octadecan-2-amine

(2S,3S,4R)-1-benzyloxy-3,4-bis-(tert-butyldimethylsilyloxy)-2-hexacosanoylamino-octadecane

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