(S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid

Base Information

• Chemical Name: (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid
• CAS No.: 910484-44-5
• Molecular Formula: C₂₅H₃₄O₅
• Molecular Weight: 414.542
• Mol file: 910484-44-5.mol

Synonyms:(S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid

Chemical Property of (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid

There total 1 articles about (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid 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: 91.0%

(3S,5S)-3-Benzyloxy-5-((S)-3-isopropenyl-6-methyl-cyclohexa-1,5-dienyl)-3-methyl-dihydro-furan-2-one + tributyl({[(methyloxy)methyl]oxy}methyl)stannane (100045-83-8) → (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid (910484-44-5)

Guidance literature:

With n-butyllithium; zinc dibromide; lithium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 18h;

DOI:10.1021/ol061072j

Reference yield: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid (910484-44-5) → (S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester (910484-36-5)

Guidance literature:

In diethyl ether; at 20 ℃;

DOI:10.1021/ol061072j

Reference yield:

(S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid (910484-44-5) → (S)-2-Benzyloxy-4-[(5R,6R)-6-formyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester (910484-46-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / diethyl ether / 20 °C

2: 98 percent / H₂ / RhCl(PPh₃)3 / benzene / 22 h / 20 °C / 1810.02 Torr

3: 90 percent / aq. HCl / propan-2-ol / 12 h / 65 °C

4: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

With hydrogenchloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; RhCl(PPh₃)3; In diethyl ether; dichloromethane; isopropyl alcohol; benzene; 4: Swern oxidation;

DOI:10.1021/ol061072j

upstream raw materials:

tributyl({[(methyloxy)methyl]oxy}methyl)stannane

Downstream raw materials:

(S)-2-Benzyloxy-4-[(5S,6R)-5-isopropenyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester

(S)-2-Benzyloxy-4-[(5R,6R)-6-formyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester

(S)-2-Benzyloxy-4-[(5R,6R)-6-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester

(S)-2-Benzyloxy-4-[(5R,6R)-5-isopropyl-6-methoxymethoxymethyl-2-methyl-cyclohex-2-en-(E)-ylidene]-2-methyl-butyric acid methyl ester