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

Base Information

• Chemical Name: (E)-2-Methyl-pentadec-2-enoic acid (1S,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-3-methoxycarbonyl-propyl ester
• CAS No.: 331626-38-1
• Molecular Formula: C₄₆H₆₄O₁₀
• Molecular Weight: 777.008
• Mol file: 331626-38-1.mol

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

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

There total 11 articles about (E)-2-Methyl-pentadec-2-enoic acid (1S,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-3-methoxycarbonyl-propyl 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:

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,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-3-methoxycarbonyl-propyl ester (331626-38-1)

Guidance literature:

Multi-step reaction with 6 steps

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

2: DCC; DMAP / CH₂Cl₂ / 20 °C

3: HCO₂H / diethyl ether / 20 °C

4: TPAP; NMO / CH₂Cl₂ / 20 °C

5: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

6: tetrahydrofuran; methanol / 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; formic acid; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol;

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,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-3-methoxycarbonyl-propyl ester (331626-38-1)

Guidance literature:

Multi-step reaction with 11 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

9: TPAP; NMO / CH₂Cl₂ / 20 °C

10: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

11: tetrahydrofuran; methanol / 20 °C

With dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; formic acid; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; [1,3-bis(diphenylphosphino)propane]dichloronickel(II); sulfuric acid; tetrabutylammomium bromide; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ja0057272

Reference yield:

allyl α,β-D-ribofuranoside (541546-94-5,773896-71-2) → (E)-2-Methyl-pentadec-2-enoic acid (1S,2R,3R)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-3-methoxycarbonyl-propyl ester (331626-38-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 4.49 g / Bu₄NBr; KOH / tetrahydrofuran; H₂O / 5 h / 90 °C

2: 87 percent / DIBAL; [1,3-bis(diphenylphosphino)propane]dichloronickel(II) / diethyl ether; hexane / 6 h / 20 °C

3: 94 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

4: 96 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

5: 85 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

6: DCC; DMAP / CH₂Cl₂ / 20 °C

7: HCO₂H / diethyl ether / 20 °C

8: TPAP; NMO / CH₂Cl₂ / 20 °C

9: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

10: tetrahydrofuran; methanol / 20 °C

With dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; formic acid; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; [1,3-bis(diphenylphosphino)propane]dichloronickel(II); tetrabutylammomium bromide; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ja0057272

upstream raw materials:

diazomethyl-trimethyl-silane

D-Ribose

allyl α,β-D-ribofuranoside

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