(E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol

Base Information

• Chemical Name: (E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol
• CAS No.: 148455-96-3
• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.51
• Mol file: 148455-96-3.mol

Synonyms:(E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol

Chemical Property of (E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol

There total 1 articles about (E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol 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)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-enoic acid ethyl ester (148455-95-2) → (E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol (148455-96-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -15 ℃; for 1h;

DOI:10.1016/S0040-4039(00)60792-X

Reference yield: 54.0%

(E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol (148455-96-3) → ((2S,3S)-3-{2-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-ethyl}-3-methyl-oxiranyl)-methanol (148455-97-4)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 3h;

DOI:10.1016/S0040-4039(00)60792-X

Reference yield:

(E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-en-1-ol (148455-96-3) → (S)-1-[(2R,5R)-5-((S)-4-Benzyloxy-1-hydroxy-1-methyl-butyl)-2-methyl-tetrahydro-furan-2-yl]-ethane-1,2-diol

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / TBHP, Ti(OiPr)4, (+)-DIPT / CH₂Cl₂ / 3 h / -20 °C

2: Amberlyst 15 A / methanol / 1 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; Amberlyst 15 A; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)60792-X

upstream raw materials:

(E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-enoic acid ethyl ester

Downstream raw materials:

((2S,3S)-3-{2-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-ethyl}-3-methyl-oxiranyl)-methanol

(S)-5-Benzyloxy-2-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-tetrahydro-furan-2-yl]-pentan-2-ol