(2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one

Base Information

• Chemical Name: (2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one
• CAS No.: 460358-62-7
• Molecular Formula: C₃₀H₃₆O₈
• Molecular Weight: 524.611

Synonyms:(2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one

Chemical Property of (2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one

There total 2 articles about (2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one 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: 67.0%

2-Hydroxy-6-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-hydroxy-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-4-methoxy-benzoic acid methyl ester (460348-38-3) → (2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.05,9]henicosa-1(21),2,11,17,19-pentaen-16-one (460358-62-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4039(02)00871-7

Reference yield: 15.0%

2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester (460348-31-6) → (2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.05,9]henicosa-1(21),2,11,17,19-pentaen-16-one (460358-62-7) + 2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-5-allyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

Guidance literature:

2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester; With bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran; at -20 - 20 ℃; for 2h;

With potassium phosphate; acetone; In tetrahydrofuran; water; at -10 - 20 ℃;

With [Pd(OAc)2+4TFP]; [Pd(OAc)2+4TFP]; In tetrahydrofuran; 1,2-dimethoxyethane; water; for 6h; Heating;

DOI:10.1016/S0040-4039(02)00871-7

Reference yield:

(2E,11Z)-(5S,9S,14S)-18-Hydroxy-20-methoxy-10-(4-methoxy-benzyloxy)-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.05,9]henicosa-1(21),2,11,17,19-pentaen-16-one (460358-62-7) → Hypothemycin (76958-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / DDQ / CH₂Cl₂; various solvent(s) / 0.5 h / 20 °C

2: 74 percent / Jones' reagent / acetone / 0.17 h / 0 °C

3: 76 percent / pTsOH / CH₂Cl₂; methanol / 0.5 h / 20 °C

4: 17 percent / MCPBA; NaHCO₃ / 4 h / -20 - 0 °C

With jones' reagent; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(02)00871-7

upstream raw materials:

2-Bromo-6-hydroxy-4-methoxy-benzoic acid (Z)-(S)-5-((4S,5S)-2,2-dimethyl-5-prop-2-ynyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-1-methyl-pent-3-enyl ester

2-Hydroxy-6-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-hydroxy-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-4-methoxy-benzoic acid methyl ester

Downstream raw materials:

Hypothemycin

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