(4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane

Base Information

• Chemical Name: (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane
• CAS No.: 162189-53-9
• Molecular Formula: C₄₂H₇₄O₆Si₂
• Molecular Weight: 731.217
• Mol file: 162189-53-9.mol

Synonyms:(4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane

Chemical Property of (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane

There total 11 articles about (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane 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:

Benzoic acid (2S,3S,8S)-1-((R)-1-benzenesulfonyl-2-{(4R,5R,6S)-6-[(S)-3-(tert-butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propyl)-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dimethoxy-8-phenyl-octyl ester → (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane (162189-53-9)

Guidance literature:

With methanol; sodium amalgam; In ethyl acetate; at -20 ℃; for 5h; Yield given;

DOI:10.1055/s-1999-3671

Reference yield:

(S)-2-{(4S,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol (220094-53-1) → (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane (162189-53-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Bu₃P / CH₂Cl₂ / 3.5 h / 0 °C

2: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) r.t., 45 min

4: 5percent Na/Hg, MeOH / ethyl acetate / 5 h / -20 °C

With methanol; sodium amalgam; tributylphosphine; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;

DOI:10.1055/s-1999-3671

Reference yield:

tert-Butyl-{(S)-3-methoxy-3-[(4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-prop-1-ynyl}-dimethyl-silane (162189-51-7) → (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane (162189-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) r.t., 45 min

3: 5percent Na/Hg, MeOH / ethyl acetate / 5 h / -20 °C

With methanol; sodium amalgam; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;

DOI:10.1055/s-1999-3671

upstream raw materials:

(2S,3S,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-8-phenyl-octanal

{(S)-3-[(4S,5R,6R)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-prop-1-ynyl}-tert-butyl-dimethyl-silane

(S)-2-{(4S,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol

(R)-2-{(4R,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

Downstream raw materials:

[(2R,3R,4S,5S,6S)-2,4-Dihydroxy-6-((E)-(1S,4R,5S,10S)-10-hydroxy-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

(1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

[(2R,3R,4S,5R,6S)-6-((E)-(1S,4R,5S,10S)-10-Acetoxy-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-2,3-dimethoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid 2-trimethylsilanyl-ethyl ester

Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester