(2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

Base Information

• Chemical Name: (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene
• CAS No.: 120269-89-8
• Molecular Formula: C₄₅H₆₄O₉
• Molecular Weight: 748.998

Synonyms:

Chemical Property of (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

There total 24 articles about (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene 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: 18.0%

(Z)-(3R,7S)-7-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1-[(3R,5S,6S)-6-((R)-1-ethyl-2-oxo-butyl)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-7-hydroxy-3-(4-methoxy-benzyloxy)-oct-1-en-4-one (126366-06-1,126454-21-5) → (2S,5R,7R,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (120269-89-8,120330-26-9) + (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (120269-89-8,120330-26-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane;

DOI:10.1248/cpb.37.1717

Reference yield: 18.0%

(Z)-(3R,7S)-7-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1-[(3R,5S,6S)-6-((R)-1-ethyl-2-oxo-butyl)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-7-hydroxy-3-(4-methoxy-benzyloxy)-oct-1-en-4-one (126366-06-1,126454-21-5) → (2S,5R,7R,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (120269-89-8,120330-26-9) + (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(R)-1-ethyl-2-oxobutyl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (120269-89-8,120330-26-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane;

DOI:10.1248/cpb.37.1717

Reference yield:

D-Glucose (2280-44-6) → (R)-4-[(2S,5R,7S,9S,10S,12R)-2-[(2R,5R,6S)-5-Ethyl-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yl]-15-(4-methoxy-benzyloxy)-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl]-hexan-3-one (120269-89-8,120330-26-9)

Guidance literature:

Multi-step reaction with 10 steps

4: 99 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

5: Ph₃P / CH₂Cl₂ / -78 °C

6: LDA / tetrahydrofuran / -30 °C

7: n-BuLi / 1.) THF, -78 deg C, 2.) oxidation

8: 1.) camphorsulfonic acid, 2.) n-Bu₄NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C

9: 88 percent / H₂ / Lindlar / methanol

10: 1.) DMSO, (COCl)2, Et₃N, 2.) CSA / 1.) CH₂Cl₂, 2.) CH₂Cl₂, room temperature

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)80703-0

upstream raw materials:

(2S,5R,6R,7Z)-8-<(2R,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

D-Glucose

(2R,3R,6S)-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol

(2R,3R,6S)-3,6-bis(tert-butyldimethylsilyloxy)-6-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-2-(4-methoxybenzyloxy)heptan-1-ol

Downstream raw materials:

salinomycin

C₅₈H₈₆O₁₃

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