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

Base Information

• Chemical Name: 2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester
• CAS No.: 909016-31-5
• Molecular Formula: C₃₇H₅₀O₆Si
• Molecular Weight: 618.886
• Mol file: 909016-31-5.mol

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

Chemical Property of 2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-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)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

There total 10 articles about 2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-hydroxy-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (202406-61-9) → 2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-31-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

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)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-31-5)

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1016/j.tet.2006.05.077

Reference yield:

(3R,5S)-1-(benzyloxy)-2,2-dimethyloct-7-ene-3,5-diol (909016-29-1) → 2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester (909016-31-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / (+/-)-camphorsulfonic acid / acetone / 19 h / 20 °C

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

3: 1.53 g / aq. NaIO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 0.5 h / 20 °C

4: 88 percent / Et₂Zn; RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.58 h / 0 °C

5: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6: PPTS / methanol / 1 h / 20 °C

7: 100 percent / imidazole / dimethylformamide / 2 h / 0 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; RhCl(PPh₃)3; camphor-10-sulfonic acid; water; diethylzinc; pyridinium p-toluenesulfonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 5: Swern oxidation;

DOI:10.1016/j.tet.2006.05.077

upstream raw materials:

tert-butylchlorodiphenylsilane

2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-hydroxy-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane

(3R,5S)-1-(benzyloxy)-2,2-dimethyloct-7-ene-3,5-diol

Downstream raw materials:

(E)-(1S,2S,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

(E)-(1S,2S,5R,11R,13R)-5-((1E,3Z)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

(E)-(1S,2S,5R,11R,13R)-13-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-5-hydroxymethyl-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-7-trityloxy-hept-3-enyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester