(E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

Base Information

• Chemical Name: (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester
• CAS No.: 331626-35-8
• Molecular Formula: C₄₅H₆₄O₉
• Molecular Weight: 748.998
• Mol file: 331626-35-8.mol

Synonyms:(E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

Chemical Property of (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester

There total 8 articles about (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester 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:

(E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-trityloxy-butyl ester → (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester (331626-35-8)

Guidance literature:

With formic acid; In diethyl ether; at 20 ℃;

DOI:10.1021/ja0057272

Reference yield:

4-Nitro-benzoic acid (1R,2S,3S)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-trityloxy-butyl ester → (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester (331626-35-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

2: DCC; DMAP / CH₂Cl₂ / 20 °C

3: HCO₂H / diethyl ether / 20 °C

With dmap; formic acid; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja0057272

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (E)-2-Methyl-pentadec-2-enoic acid (1S,2S,3S)-4-hydroxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-butyl ester (331626-35-8)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂SO₄ / 12 h / 4 °C

2: 4.49 g / Bu₄NBr; KOH / tetrahydrofuran; H₂O / 5 h / 90 °C

3: 87 percent / DIBAL; [1,3-bis(diphenylphosphino)propane]dichloronickel(II) / diethyl ether; hexane / 6 h / 20 °C

4: 94 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

5: 96 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

6: 85 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

7: DCC; DMAP / CH₂Cl₂ / 20 °C

8: HCO₂H / diethyl ether / 20 °C

With dmap; potassium hydroxide; formic acid; [1,3-bis(diphenylphosphino)propane]dichloronickel(II); sulfuric acid; tetrabutylammomium bromide; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;

DOI:10.1021/ja0057272

upstream raw materials:

D-Ribose

allyl α,β-D-ribofuranoside

(2S,3R,4R)-2,3,5-tris(4-methoxybenzyloxy)-1,4-pentanediol

allyl 2,3,5-tri-O-p-methoxybenzyl-D-ribofuranose

Downstream raw materials:

(E)-2-Methyl-pentadec-2-enoic acid (1S,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-3-methoxycarbonyl-propyl ester