methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate

Base Information

• Chemical Name: methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate
• CAS No.: 145762-65-8
• Molecular Formula: C₂₀H₂₈O₈S
• Molecular Weight: 428.504
• Mol file: 145762-65-8.mol

Synonyms:methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate

Chemical Property of methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate

There total 10 articles about methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate 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: 100.0%

methyl (5Z)-4-benzyloxy-8-hydroxy-2-methoxycarbonyl-6-methyloct-5-enoate (145762-63-6) + methanesulfonyl chloride (124-63-0) → methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate (145762-65-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1139/v92-297

Reference yield:

(3Z)-2-benzyloxy-6-<(2-tetrahydropyranyl)oxy>-4-methylhex-3-en-1-ol (122598-89-4) → methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate (145762-65-8)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) sodium hydride, 2.) potassium iodide / 1.) THF, DMF, room temperature, 0.5 h, 2.) reflux, 48 h

3: 88 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / Heating

4: 100 percent / triethylamine / CH₂Cl₂ / 0 °C

With pyridinium p-toluenesulfonate; sodium hydride; triethylamine; potassium iodide; In methanol; dichloromethane;

DOI:10.1139/v92-297

Reference yield:

3-benzyloxy-3-<(tert-butyldiphenylsilyl)oxy>-propan-1-ol (145842-04-2) → methyl (5Z)-4-benzyloxy-8-methanesulfonyloxy-2-methoxycarbonyl-6-methyloct-5-enoate (145762-65-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 deg C to 10 deg C, 0.5 h

2: 1.) butyllithium / 1.) THF, hexane, -78 deg C to 0 deg C, ca. 0.5 h, 2.) THF, 0 deg C, 10 min

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) sodium hydride, 2.) potassium iodide / 1.) THF, DMF, room temperature, 0.5 h, 2.) reflux, 48 h

6: 88 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / Heating

7: 100 percent / triethylamine / CH₂Cl₂ / 0 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; potassium iodide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1139/v92-297

upstream raw materials:

methyl (5Z)-4-benzyloxy-8-hydroxy-2-methoxycarbonyl-6-methyloct-5-enoate

methanesulfonyl chloride

(3Z)-2-benzyloxy-6-<(2-tetrahydropyranyl)oxy>-4-methylhex-3-en-1-ol

3-benzyloxy-3-<(tert-butyldiphenylsilyl)oxy>-propan-1-ol

Downstream raw materials:

methyl (5Z,11Z,13E)-7-benzyloxy-15-chloro-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

methyl (5Z,11Z,13E)-7-benzyloxy-15-hydroxy-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

methyl (5Z,11Z,13E)-7-benzyloxy-15-<(tert-butyldiphenylsilyl)oxy>-5-methyl-2,9,9-trimethoxycarbonylpentadeca-5,11,13-trienoate

(3E,5Z,11Z)-10-Benzyloxy-12-methyl-cyclotetradeca-3,5,11-triene-1,1,8,8-tetracarboxylic acid tetramethyl ester