(5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one
• CAS No.: 870075-29-9
• Molecular Formula: C₅₃H₉₄O₈Si₂
• Molecular Weight: 915.496
• Mol file: 870075-29-9.mol

Synonyms:(5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one

Chemical Property of (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one

There total 11 articles about (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-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: 50.0%

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde (853055-22-8) + [(5Z,13Z)-(2R,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadeca-5,13-dienyl]-triphenyl-phosphonium; iodide → (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one (870075-29-9)

Guidance literature:

With methyllithium;

DOI:10.1021/ol052070m

Reference yield:

(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-5-methyl-5,6-dihydro-pyran-2-one (837383-29-6) → (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one (870075-29-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

2: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

3: 50 percent / MeLi

With methyllithium; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; palladium dihydroxide; In dichloromethane; ethyl acetate; 2: Dess-Martin oxidation / 3: Wittig reaction;

DOI:10.1021/ol052070m

Reference yield:

(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-trityloxy-heptanal (850211-67-5) → (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one (870075-29-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran / 0.67 h / 20 °C

1.2: tetrahydrofuran / -78 - -10 °C

2.1: formic acid / diethyl ether / 12 h / 20 °C

2.2: 87 percent / K₂CO₃ / methanol / 0.08 h

3.1: 90 percent / I₂; PPh₃

4.1: 90 percent / aq. HCl

5.1: I₂; PPh₃; imidazole

6.1: DIPEA / 100 °C

7.1: 50 percent / MeLi

With 1H-imidazole; hydrogenchloride; n-butyllithium; formic acid; methyllithium; iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; 4.1: Suzuki coupling / 8.1: Wittig reaction;

DOI:10.1021/ol052070m

upstream raw materials:

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((2S,3R)-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-propionaldehyde

(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-5-methyl-5,6-dihydro-pyran-2-one

(2R,3R,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-trityloxy-heptanal

(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-5-methyl-tetrahydro-pyran-2-one