(2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol

Base Information

• Chemical Name: (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol
• CAS No.: 334518-79-5
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 334518-79-5.mol

Synonyms:(2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol

Chemical Property of (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol

There total 8 articles about (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)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:

(Z)-(4S,5S)-4-Benzyloxy-6-iodo-4-methyl-hex-2-ene-1,5-diol → (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol (334518-79-5)

Guidance literature:

With potassium hydroxide; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1016/S0040-4020(00)01117-0

Reference yield:

2,3,6-trideoxy-6-iodo-4-O-benzyl-4-C-methyl-D-erythro-hex-2-enopyranose → (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol (334518-79-5) + (Z)-(4S,5S)-4-Benzyloxy-6-iodo-4-methyl-hex-2-ene-1,5-diol

Guidance literature:

With lithium borohydride; In octanol; at 20 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(00)01117-0

Reference yield:

methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (33647-80-2) → (2Z,4S)-4-[(2R)-oxiran-2-yl]-4-(phenylmethoxy)pent-2-en-1-ol (334518-79-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 1 h / 20 °C

2: 80 percent / diethyl ether / 7 h / 0 - 20 °C

3: 77 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 10 h / 20 °C

4: 84 percent / acetic acid / dioxane; H₂O / 4.5 h / Heating

5: lithium borohydride / octan-1-ol / 24 h / 20 °C

With lithium borohydride; methyltriphenoxyphosphonium iodide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; octanol; water; N,N-dimethyl-formamide; 2: Grignard reaction;

DOI:10.1016/S0040-4020(00)01117-0

upstream raw materials:

methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

methyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside

methyl 2,3,6-trideoxy-6-iodo-α-D-glycero-hex-2-enopyranosid-4-ulose

methyl 2,3,6-trideoxy-6-iodo-4-C-methyl-α-D-erythro-hex-2-enopyranoside