(Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester
• CAS No.: 151378-51-7
• Molecular Formula: C₃₂H₅₁NO₅
• Molecular Weight: 529.761
• Mol file: 151378-51-7.mol

Synonyms:

Chemical Property of (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

There total 24 articles about (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester 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: 34.0%

(E)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester (149298-92-0) → (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester (151378-51-7)

Guidance literature:

In acetone; at 0 ℃; Irradiation;

DOI:10.1016/S0040-4039(00)60377-5

Reference yield:

(1''S,2S,2'R,3'S,5'R)-(+)-2-[Tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]-2-methylethanol (103576-56-3) → (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester (151378-51-7)

Guidance literature:

Multi-step reaction with 13 steps

1: Bu₃P, pyridine

2: mcpba / CH₂Cl₂

3: 1.) n-BuLi / 1.) THF

4: NaN(TMS)2

5: AIBN / toluene

6: (i-Bu)2AlH (DIBALH)

7: DMSO, (COCl)2, Et₃N / CH₂Cl₂

8: NaClO₂

10: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min

11: pyridine, DMAP

12: DBU / Ambient temperature

13: 34 percent / acetone / 0 °C / Irradiation

With pyridine; dmap; sodium chlorite; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4039(00)60377-5

Reference yield:

(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile (148766-02-3) → (Z)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester (151378-51-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

2: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min

3: pyridine, DMAP

4: DBU / Ambient temperature

5: 34 percent / acetone / 0 °C / Irradiation

With pyridine; dmap; oxalyl dichloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In dichloromethane; acetone;

DOI:10.1016/S0040-4039(00)60377-5

upstream raw materials:

(E)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

(1''S,2S,2'R,3'S,5'R)-(+)-2-[Tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]-2-methylethanol

(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

(S)-2-((1R,2S,6R)-2-Formyl-6-methyl-cyclohexyl)-propionitrile

Downstream raw materials:

C₄₂H₇₂O₉Si

(S)-2-{(1S,2S,6R)-2-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-propenyl]-6-methyl-cyclohexyl}-propionaldehyde

tetronasin sodium salt