(2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-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-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene
• CAS No.: 126365-74-0
• Molecular Formula: C₃₇H₅₈O₈
• Molecular Weight: 630.863

Synonyms:

Chemical Property of (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-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:

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Useful:

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

There total 3 articles about (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-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:

20-acetoxysalinomycin methyl ester (60851-36-7) → (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (126365-74-0,126454-15-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / 200 °C / 0.5 Torr

2: 100 percent / CSA / CH₂Cl₂ / Ambient temperature

3: 96 percent / Red-Al / toluene / 0.5 h / -70 °C

4: 1) NaH / 1) THF, DMF, 45 min, RT, 2) THF, DMF, 3 h

With camphor-10-sulfonic acid; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; toluene;

DOI:10.1248/cpb.37.1726

Reference yield:

(2S,5S,7S,9S,10S,12R,13Z,15R)-15-acetoxy-2-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl)-9-((R)-1-ethyl-2-oxobutyl)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene (110653-78-6,126454-01-1,126454-06-6) → (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (126365-74-0,126454-15-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Red-Al / toluene / 0.5 h / -70 °C

2: 1) NaH / 1) THF, DMF, 45 min, RT, 2) THF, DMF, 3 h

With sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene;

DOI:10.1248/cpb.37.1726

Reference yield:

(2S,5S,7R,9S,10S,12R,13Z,15R)-15-acetoxy-2-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl)-9-((R)-1-ethyl-2-oxobutyl)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene (110653-78-6,126454-01-1,126454-06-6) → (2S,5S,7S,9S,10S,12R,13Z,15R)-9-<(1S,2RS)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene (126365-74-0,126454-15-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CSA / CH₂Cl₂ / Ambient temperature

2: 96 percent / Red-Al / toluene / 0.5 h / -70 °C

3: 1) NaH / 1) THF, DMF, 45 min, RT, 2) THF, DMF, 3 h

With camphor-10-sulfonic acid; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; toluene;

DOI:10.1248/cpb.37.1726

upstream raw materials:

20-acetoxysalinomycin methyl ester

(2S,5S,7R,9S,10S,12R,13Z,15R)-15-acetoxy-2-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl)-9-((R)-1-ethyl-2-oxobutyl)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

(2S,5S,7S,9S,10S,12R,13Z,15R)-15-acetoxy-2-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl)-9-((R)-1-ethyl-2-oxobutyl)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene

Downstream raw materials:

(2S,5S,7S,9S,10S,12R,13RS,14SR,15R)-9-<(1S)-1-ethyl-2-hydroxybutyl>-2-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadecan-13,14-diol

(2S,3R,6R)-3-Ethyl-6-{(2S,5S)-5-[(2S,3R,5S,6S)-6-((S)-1-ethyl-2-hydroxy-butyl)-2-hydroxymethyl-3,5-dimethyl-tetrahydro-pyran-2-yloxy]-5-[(R)-2-hydroxy-1-(4-methoxy-benzyloxy)-ethyl]-2-methyl-tetrahydro-furan-2-yl}-2-methyl-tetrahydro-pyran-3-ol

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