(1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol

Base Information

• Chemical Name: (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol
• CAS No.: 1335029-13-4
• Molecular Formula: C₃₅H₅₂O₇
• Molecular Weight: 584.794

Synonyms:

Chemical Property of (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol

Chemical Property:

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Safty Information:

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Technology Process of (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol

There total 13 articles about (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-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:

(2S,6R,11S)-2-((R)-1-bromopropan-2-yl)-11-methyl-1,7-dioxaspiro[5.5]undecane (1335028-88-0) + C22H28O5 (1335028-87-9) → (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol (1335029-13-4) + (1S,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol (1335029-02-1)

Guidance literature:

(2S,6R,11S)-2-((R)-1-bromopropan-2-yl)-11-methyl-1,7-dioxaspiro[5.5]undecane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 25 ℃; for 0.5h;

C₂₂H₂₈O₅; In diethyl ether; pentane; at -78 ℃; for 0.5h;

With water; ammonium chloride; In diethyl ether; pentane; at -78 - 25 ℃;

DOI:10.1002/anie.201101741

Reference yield:

(3S,4S)-3,5-bis(benzyloxy)-4-methylpentanal (1335029-00-9) → (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol (1335029-13-4) + (1S,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol (1335029-02-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.25 h / 25 °C

1.2: 16 h / 25 °C

2.1: 20 % Pd(OH)2/C; hydrogen / ethanol / 15 h / 760.05 Torr

3.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 16 h

4.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 - 25 °C

4.2: 0.5 h / -78 °C

4.3: -78 - 25 °C

With carbon tetrabromide; 20 % Pd(OH)2/C; hydrogen; tert.-butyl lithium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In diethyl ether; ethanol; dichloromethane; acetonitrile; pentane; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1002/anie.201101741

Reference yield:

(S)-2-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol (1039455-95-2) → (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol (1335029-13-4) + (1S,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol (1335029-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 16 h

2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 - 25 °C

2.2: 0.5 h / -78 °C

2.3: -78 - 25 °C

With carbon tetrabromide; tert.-butyl lithium; triethylamine; triphenylphosphine; In diethyl ether; dichloromethane; pentane;

DOI:10.1002/anie.201101741

upstream raw materials:

(S)-2-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

(3S,4S)-3,5-bis(benzyloxy)-4-methylpentan-1-yl 4-methoxybenzyl ether

C₁₄H₂₂O₄

(3S,4S)-3,5-bis(benzyloxy)-4-methylpentan-1-ol

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