(Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol

Base Information

• Chemical Name: (Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol
• CAS No.: 869338-49-8
• Molecular Formula: C₁₆H₂₃IO₃
• Molecular Weight: 390.261
• Mol file: 869338-49-8.mol

Synonyms:(Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol

Chemical Property of (Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol

There total 1 articles about (Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-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: 95.0%

tert-Butyl-{(Z)-(1R,2S)-4-iodo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyloxy}-dimethyl-silane → (Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol (869338-49-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 20 ℃; for 4h;

DOI:10.1021/ol051691c

Reference yield: 71.0%

(Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol (869338-49-8) + Chloroiodomethane (593-71-5) → (2S,3R,4S)-4-((1R,2R)-2-Iodo-cyclopropyl)-1-(4-methoxy-benzyloxy)-2-methyl-pentan-3-ol (869338-32-9)

Guidance literature:

With diethylzinc; In 1,2-dichloro-ethane; at 20 ℃; for 3h;

DOI:10.1021/ol051691c

Reference yield:

(Z)-(2S,3R,4S)-6-Iodo-1-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-en-3-ol (869338-49-8) → 1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene (869338-46-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 71 percent / Et₂Zn / 1,2-dichloro-ethane / 3 h / 20 °C

2.1: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

3.1: 90 percent / DDQ; H₂O / CH₂Cl₂ / 0 - 20 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -30 °C

5.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C / y

5.2: 2-ThCuCNLi / tetrahydrofuran; pentane / 0.5 h / -78 - -20 °C

5.3: 61 percent / tetrahydrofuran; pentane / 23 h / -40 - 0 °C

6.1: 92 percent / DIBAL

7.1: 96 percent / Dess-Martin periodinane

8.1: CrCl₂

8.2: 91 percent / KOH / methanol

With 2,6-dimethylpyridine; chromium dichloride; water; tert.-butyl lithium; diethylzinc; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; pentane;

DOI:10.1021/ol051691c

Downstream raw materials:

(2S,3R,4S)-4-((1R,2R)-2-Iodo-cyclopropyl)-1-(4-methoxy-benzyloxy)-2-methyl-pentan-3-ol

1-[(2S,3R,4S)-4-((1R,2R)-2-Iodo-cyclopropyl)-3-methoxymethoxy-2-methyl-pentyloxymethyl]-4-methoxy-benzene

(2S,3R,4S)-4-{(1S,2S)-2-[(Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-deca-7,9-dienyl]-cyclopropyl}-3-methoxymethoxy-2-methyl-pentan-1-ol

(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1S,2S)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanal