[(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester
• CAS No.: 120927-67-5
• Molecular Formula: C₃₉H₅₂O₈Si
• Molecular Weight: 676.923

Synonyms:

Chemical Property of [(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

There total 24 articles about [(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl 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:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) → [(1S,3S,4S,5R,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120927-67-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

5: 92 percent / imidazole / dimethylformamide / Ambient temperature

6: 82 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

7: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

8: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

9: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

10: n-Bu₃SnH, AIBN / toluene / Heating

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo00028a033

Reference yield:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) → [(1S,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120927-67-5,120964-40-1,120964-41-2,120964-42-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

5: 92 percent / imidazole / dimethylformamide / Ambient temperature

6: 82 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

7: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

8: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

9: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

10: n-Bu₃SnH, AIBN / toluene / Heating

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo00028a033

Reference yield:

benzyl bromide (100-39-0) → [(1S,3S,4S,5R,6R,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120927-67-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

5: 92 percent / imidazole / dimethylformamide / Ambient temperature

6: 82 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

7: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

8: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

9: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

10: n-Bu₃SnH, AIBN / toluene / Heating

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo00028a033

upstream raw materials:

Ethyl (α-p-Methoxybenzyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-D-manno-D-glycero-non-7-eno-1,5-pyranos)uronate

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

benzyl bromide

3,4-di-O-benzyl-D-glucal

Downstream raw materials:

(1R,2S,6S,7S,8S,10S,11R)-10,11-Bis-benzyloxy-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[5.2.2.0^2,6]undecan-4-one

[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

(1R,2R,6R,7S,8S,10S,11R)-10,11-Bis-benzyloxy-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[5.2.2.0^2,6]undecan-4-one

[(1R,3S,4S,5S,6R,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

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