(E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.0^3,7]hexacos-16-ene-2,15,21-trione

Base Information

• Chemical Name: (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.0^3,7]hexacos-16-ene-2,15,21-trione
• CAS No.: 136358-39-9
• Molecular Formula: C₄₂H₆₇NO₁₁Si
• Molecular Weight: 790.08

Synonyms:

Chemical Property of (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.0^3,7]hexacos-16-ene-2,15,21-trione

Chemical Property:

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Safty Information:

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Technology Process of (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.0^3,7]hexacos-16-ene-2,15,21-trione

There total 13 articles about (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.0^3,7]hexacos-16-ene-2,15,21-trione 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: 84.0%

(S)-1-[(4S,5R)-5-{(1R,3S,4S,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(diethoxy-phosphoryl)-acetoxy]-3,5-dimethoxy-1,7-dimethyl-octyl}-2-(4-methoxy-phenyl)-[1,3]dioxolane-4-carbonyl]-piperidine-2-carboxylic acid 2,2-dimethyl-3-oxo-propyl ester → (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.03,7]hexacos-16-ene-2,15,21-trione (136358-39-9,136457-99-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride;

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.03,7]hexacos-16-ene-2,15,21-trione (136358-39-9,136457-99-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 - 20 °C

2: 60.4 percent / dihydroquinidine acetate, OsO₄ / toluene / 5 h

3: 96 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 2 h

4: 80 percent / 4A molecular sieves, camphorsulfonic acid / benzene; tetrahydrofuran / 2 h / Ambient temperature

5: 95 percent / dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.33 h

6: 90.8 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / -15 - -10 °C

7: (benzotriazolyl-1-oxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP)

8: Dess-Martin periodinate

9: 84 percent / LiCl, diazobicycloundecene (DBU)

With 2,6-dimethylpyridine; lithium hydroxide; osmium(VIII) oxide; hydroquinidine acetate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; benzene;

Reference yield:

<2R,S,3R,5S,6S,6(1S,2S)>-2-hydroxy-6-<2-(benzyloxy)-1-methoxy-3-methylbutyl>-5-methoxy-3-methyltetrahydropyran (136358-53-7,136358-54-8) → (E)-(3S,7R,8R,10S,11S,12S,13S,22S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-isopropyl-10,12-dimethoxy-5-(4-methoxy-phenyl)-8,18,18-trimethyl-4,6,14,20-tetraoxa-1-aza-tricyclo[20.4.0.03,7]hexacos-16-ene-2,15,21-trione (136358-39-9,136457-99-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 73.5 percent / acetonitrile / 72 h / Heating

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 - 20 °C

3: 60.4 percent / dihydroquinidine acetate, OsO₄ / toluene / 5 h

4: 96 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 2 h

5: 80 percent / 4A molecular sieves, camphorsulfonic acid / benzene; tetrahydrofuran / 2 h / Ambient temperature

6: 95 percent / dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.33 h

7: 90.8 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / -15 - -10 °C

8: (benzotriazolyl-1-oxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP)

9: Dess-Martin periodinate

10: 84 percent / LiCl, diazobicycloundecene (DBU)

With 2,6-dimethylpyridine; lithium hydroxide; osmium(VIII) oxide; hydroquinidine acetate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene;

upstream raw materials:

p-Anisaldehyde dimethyl acetal

t-butyldimethylsiyl triflate

<2R,S,3R,5S,6S,6(1S,2S)>-2-hydroxy-6-<2-(benzyloxy)-1-methoxy-3-methylbutyl>-5-methoxy-3-methyltetrahydropyran

(2S,3R,4R,6S,7S,8S,9S)-7-<(tert-butyldimethylsilyl)oxy>-2,3,9-trihydroxy-6,8-dimethoxy-4,10-dimethylundecanoic acid methyl ester

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