(1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1^1,5]octadecane-7,11-dione

Base Information

• Chemical Name: (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1^1,5]octadecane-7,11-dione
• CAS No.: 128308-14-5
• Molecular Formula: C₄₆H₆₀O₉
• Molecular Weight: 756.977

Synonyms:(1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1^1,5]octadecane-7,11-dione

Chemical Property of (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1^1,5]octadecane-7,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1^1,5]octadecane-7,11-dione

There total 5 articles about (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.1^1,5]octadecane-7,11-dione 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: 23.0%

{(2S,3R,6R,8R,9S,10S)-8-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-10-hydroxy-3,5,5,9-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid (1R,2R)-2-benzyloxy-1-tert-butylsulfanylcarbonylmethyl-propyl ester (128308-13-4) → (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.11,5]octadecane-7,11-dione (128308-14-5)

Guidance literature:

With disodium hydrogenphosphate; silver trifluoromethanesulfonate; In benzene; for 27h; Ambient temperature;

DOI:10.1016/S0040-4039(00)70661-7

Reference yield:

(3R,4R)-4-Benzyloxy-3-hydroxy-pentanethioic acid S-tert-butyl ester (128440-08-4) → (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.11,5]octadecane-7,11-dione (128308-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / DCC / DMAP / diethyl ether / 5 h / Ambient temperature

2: 23 percent / AgOTf, Na₂HPO₄ / benzene / 27 h / Ambient temperature

With disodium hydrogenphosphate; silver trifluoromethanesulfonate; dicyclohexyl-carbodiimide; dmap; In diethyl ether; benzene;

DOI:10.1016/S0040-4039(00)70661-7

Reference yield:

{(2S,3R,6R,8R,9S,10S)-8-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-10-hydroxy-3,5,5,9-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid (128308-12-3) → (1R,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.11,5]octadecane-7,11-dione (128308-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / DCC / DMAP / diethyl ether / 5 h / Ambient temperature

2: 23 percent / AgOTf, Na₂HPO₄ / benzene / 27 h / Ambient temperature

With disodium hydrogenphosphate; silver trifluoromethanesulfonate; dicyclohexyl-carbodiimide; dmap; In diethyl ether; benzene;

DOI:10.1016/S0040-4039(00)70661-7

upstream raw materials:

{(2S,3R,6R,8R,9S,10S)-8-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-10-hydroxy-3,5,5,9-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid (1R,2R)-2-benzyloxy-1-tert-butylsulfanylcarbonylmethyl-propyl ester

(3R,4R)-4-Benzyloxy-3-hydroxy-pentanethioic acid S-tert-butyl ester

{(2S,3R,6R,8R,9S,10S)-8-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-10-hydroxy-3,5,5,9-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid

{(2S,3R,6R,8R,9S,10S)-8-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-10-hydroxy-3,5,5,9-tetramethyl-1,7-dioxa-spiro[5.5]undec-2-yl}-acetic acid methyl ester

Downstream raw materials:

3-deoxydebromoaplysiatoxin

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