((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester
• CAS No.: 914083-48-0
• Molecular Formula: C₃₄H₅₉NO₇Si
• Molecular Weight: 621.93

Synonyms:((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

Chemical Property of ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

There total 23 articles about ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester 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: 82.0%

((1S,2S)-2,3-Dihydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (914083-46-8) + tert-butyldimethylsilyl chloride (18162-48-6) → ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (914083-48-0)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane;

DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

(S)-8-Benzyloxy-3-methyl-octanal (914083-14-0) → ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (914083-48-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 86 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

2.1: 90 percent / Ph₃P / benzene / 20 °C

3.1: AD mix-αMeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

4.1: CSA / CH₂Cl₂ / 1 h

5.1: 87 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

6.1: 80 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: 85 percent / CSA / CH₂Cl₂ / 20 °C

8.1: pyridine / CH₂Cl₂ / -10 °C

9.1: Bu₄NBr / CH₂Cl₂ / 20 °C

10.1: 82 percent / NaN₃ / dimethylformamide / 4 h / 65 °C

11.1: 92 percent / H₂ / Pd(OH)2/C / methanol

12.1: 88 percent / IBX / dimethylsulfoxide; tetrahydrofuran / 3 h

13.1: n-BuLi / tetrahydrofuran / 12 h / 0 - 20 °C

13.2: Pd(CH₃CN)2Cl₂ / CH₂Cl₂ / 20 °C

14.1: 75 percent / PPTS / methanol / 12 h / 45 °C

15.1: 82 percent / imidazole; DMAP / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; sodium azide; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; triphenylphosphine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 3.1: Sharpless asymmetric dihydroxylation / 5.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

(S)-6-Methyl-8-(tetrahydro-pyran-2-yloxy)-octan-1-ol (914498-66-1) → ((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (914083-48-0)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 90 percent / NaH / tetrahydrofuran / 0 - 20 °C

2.1: 93 percent / p-TSA / methanol / 2 h / 20 °C

3.1: 95 percent / IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

4.1: 86 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

5.1: 90 percent / Ph₃P / benzene / 20 °C

6.1: AD mix-αMeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

7.1: CSA / CH₂Cl₂ / 1 h

8.1: 87 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

9.1: 80 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

10.1: 85 percent / CSA / CH₂Cl₂ / 20 °C

11.1: pyridine / CH₂Cl₂ / -10 °C

12.1: Bu₄NBr / CH₂Cl₂ / 20 °C

13.1: 82 percent / NaN₃ / dimethylformamide / 4 h / 65 °C

14.1: 92 percent / H₂ / Pd(OH)2/C / methanol

15.1: 88 percent / IBX / dimethylsulfoxide; tetrahydrofuran / 3 h

16.1: n-BuLi / tetrahydrofuran / 12 h / 0 - 20 °C

16.2: Pd(CH₃CN)2Cl₂ / CH₂Cl₂ / 20 °C

17.1: 75 percent / PPTS / methanol / 12 h / 45 °C

18.1: 82 percent / imidazole; DMAP / CH₂Cl₂

With pyridine; 1H-imidazole; dmap; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; sodium azide; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 6.1: Sharpless asymmetric dihydroxylation / 8.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetlet.2006.07.107

upstream raw materials:

((1S,2S)-2,3-Dihydroxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

tert-butyldimethylsilyl chloride

(S)-8-Benzyloxy-3-methyl-octanal

(S)-8-Benzyloxy-3-methyl-octan-1-ol

Downstream raw materials:

((1S,2S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

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