(2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol

Base Information

• Chemical Name: (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol
• CAS No.: 152386-86-2
• Molecular Formula: C₃₁H₅₂O₄
• Molecular Weight: 488.751
• Mol file: 152386-86-2.mol

Synonyms:(2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol

Chemical Property of (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol

There total 11 articles about (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol 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:

myristylaldehyde (124-25-4,511542-15-7) + (2R,3S)-3-O-(4-methoxybenzyl)-1,2-O-(3-pentylidene)-4-(1-phenyl-1H-tetrazol-5-sulfonyl)-1,2,3-butantriol (452082-47-2) → (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol (152386-86-2) + (2R,3R)-1,2-O-pentylidene-3-(4-methoxybenzyl)-(4Z)-octadecen-1,2,3-triol

Guidance literature:

With potassium hexamethylsilazane; In 1,2-dimethoxyethane; toluene; at -55 ℃; for 0.25h;

DOI:10.1016/S0040-4020(02)00418-0

Reference yield:

(2S)-2-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-2-(4-methoxybenzyloxy)-acetaldehyde (152386-87-3) + 5-(tetradecane-1-sulfonyl)-1-phenyl-1H-tetrazoe (452082-46-1) → (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol (152386-86-2) + (2R,3R)-1,2-O-pentylidene-3-(4-methoxybenzyl)-(4Z)-octadecen-1,2,3-triol

Guidance literature:

With potassium hexamethylsilazane; In 1,2-dimethoxyethane; toluene; at -55 - 20 ℃;

DOI:10.1016/S0040-4020(02)00418-0

Reference yield:

(1R,2S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)ethan-1-ol (152386-85-1) → (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol (152386-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Ph₃P; DEAD / tetrahydrofuran / 1 h / 40 °C

2: 80 percent / MCPBA / CH₂Cl₂ / 24 h / 20 °C

3: KHMDS / toluene; 1,2-dimethoxy-ethane / 0.25 h / -55 °C

With potassium hexamethylsilazane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00418-0

upstream raw materials:

(n-tetradecyl)triphenylphosphonium bromide

(2S)-2-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-2-(4-methoxybenzyloxy)-acetaldehyde

myristylaldehyde

(2R,3S)-3-O-(4-methoxybenzyl)-1,2-O-(3-pentylidene)-4-(1-phenyl-1H-tetrazol-5-sulfonyl)-1,2,3-butantriol

Downstream raw materials:

(2R,3R,4E)-3-(4'-methoxybenzyloxy)-4-octadecene-1,2-diol

2-azido-sphingosine

(2S,3R,4E)-2-azido-3-(4-methoxybenzyl)-4-octadecen-1,3-diol

(2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol