2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

Base Information

• Chemical Name: 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester
• CAS No.: 909016-43-9
• Molecular Formula: C₄₈H₇₆O₇Si₃
• Molecular Weight: 849.384
• Mol file: 909016-43-9.mol

Synonyms:2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

Chemical Property of 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

There total 20 articles about 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl 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: 81.0%

(3E,7E)-(R)-8-Iodo-7-methyl-5-triethylsilanyloxy-1-trimethylsilanyl-octa-3,7-dien-1-yne (909016-27-9) + 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (202406-63-1) → 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-43-9)

Guidance literature:

With chromium dichloride; nickel dichloride; In dimethyl sulfoxide; at 20 ℃; for 120h;

DOI:10.1016/j.tet.2006.05.077

Reference yield:

3-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propane-1,2-diol → 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-43-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.53 g / aq. NaIO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 0.5 h / 20 °C

2: 88 percent / Et₂Zn; RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.58 h / 0 °C

3: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4: PPTS / methanol / 1 h / 20 °C

5: 100 percent / imidazole / dimethylformamide / 2 h / 0 °C

6: 96 percent / H₂ / Pd(OH)2/C / dioxane / 2 h / 20 °C

7: 95 percent / SO₃*py; DMSO; Et₃N / 1 h / 20 °C

8: 81 percent / NiCl₂; CrCl₂ / dimethylsulfoxide / 120 h / 20 °C

With 1H-imidazole; chromium dichloride; sodium periodate; oxalyl dichloride; pyridine-SO₃ complex; RhCl(PPh₃)3; hydrogen; diethylzinc; pyridinium p-toluenesulfonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; nickel dichloride; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 3: Swern oxidation / 8: Nozaki-Hiyama-Kishi reaction;

DOI:10.1016/j.tet.2006.05.077

Reference yield:

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane (111080-21-8) → 2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-43-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C

2.1: (CF₃CO₂)2IPh / methanol / 0.75 h / 0 °C

2.2: 77 percent / aq. AcOH / tetrahydrofuran / 0.25 h / 20 °C

3.1: 86 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / -40 - -30 °C

4.1: 97 percent / (+/-)-camphorsulfonic acid / acetone / 19 h / 20 °C

5.1: OsO₄; N-methylmorpholine-N-oxide; H₂O / 2-methyl-propan-2-ol; acetone / 2 h / 20 °C

6.1: 1.53 g / aq. NaIO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 0.5 h / 20 °C

7.1: 88 percent / Et₂Zn; RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.58 h / 0 °C

8.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

9.1: PPTS / methanol / 1 h / 20 °C

10.1: 100 percent / imidazole / dimethylformamide / 2 h / 0 °C

11.1: 96 percent / H₂ / Pd(OH)2/C / dioxane / 2 h / 20 °C

12.1: 95 percent / SO₃*py; DMSO; Et₃N / 1 h / 20 °C

13.1: 81 percent / NiCl₂; CrCl₂ / dimethylsulfoxide / 120 h / 20 °C

With 1H-imidazole; chromium dichloride; sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; RhCl(PPh₃)3; camphor-10-sulfonic acid; water; hydrogen; diethylzinc; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; nickel dichloride; tetramethylammonium triacetoxyborohydride; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 8.1: Swern oxidation / 13.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1016/j.tet.2006.05.077

upstream raw materials:

(3E,7E)-(R)-8-Iodo-7-methyl-5-triethylsilanyloxy-1-trimethylsilanyl-octa-3,7-dien-1-yne

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

(2R,4E)-5-iodo-4-methylpent-4-ene-1,2-diol

(E)-(R)-5-Iodo-4-methyl-2-triethylsilanyloxy-pent-4-enal