<3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester

Base Information

• Chemical Name: <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester
• CAS No.: 104410-88-0
• Molecular Formula: C₃₁H₄₉NO₈SSi₂
• Molecular Weight: 651.969
• Mol file: 104410-88-0.mol

Synonyms:

Chemical Property of <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester

There total 16 articles about <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl 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:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester (104410-88-0,109215-74-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 20percent DIBAL-H / toluene; hexane / 4 h / -78 °C

3: 80 percent / tetrahydrofuran / 24 h / Heating

4: 96 percent / triethylamine / benzene / 1.) 0 deg C, 5 min, 2.) RT, 15 min, 3.) 55 deg C, 6 h

5: 64 percent / benzene / 24 h / 110 °C / sealed tube

6: 1.) 1.0M borane 2.) 30percent H₂O₂, 2N NaOH / 1.) THF, 0 deg C, 1.5 h, 2.) 0 deg C, 0,5 h

7: 52percent HF / tetrahydrofuran; H₂O / 24 h / Ambient temperature

8: imidazole / dimethylformamide / 48 h / 55 °C

9: 94 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O / 24 h / Ambient temperature

10: tetrahydrofuran / 5 h / Heating

With 1H-imidazole; sodium hydroxide; hydrogen fluoride; borane; dihydrogen peroxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja00251a021

Reference yield:

N-benzyloxycarbonyl-L-treonine (19728-63-3) → <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester (104410-88-0,109215-74-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / conc. sulfuric acid / 36 h / Ambient temperature

2: 99 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

3: 20percent DIBAL-H / toluene; hexane / 4 h / -78 °C

4: 80 percent / tetrahydrofuran / 24 h / Heating

5: 96 percent / triethylamine / benzene / 1.) 0 deg C, 5 min, 2.) RT, 15 min, 3.) 55 deg C, 6 h

6: 64 percent / benzene / 24 h / 110 °C / sealed tube

7: 1.) 1.0M borane 2.) 30percent H₂O₂, 2N NaOH / 1.) THF, 0 deg C, 1.5 h, 2.) 0 deg C, 0,5 h

8: 52percent HF / tetrahydrofuran; H₂O / 24 h / Ambient temperature

9: imidazole / dimethylformamide / 48 h / 55 °C

10: 94 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O / 24 h / Ambient temperature

11: tetrahydrofuran / 5 h / Heating

With 1H-imidazole; sodium hydroxide; sulfuric acid; hydrogen fluoride; borane; dihydrogen peroxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja00251a021

Reference yield:

(2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (104410-78-8) → <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester (104410-88-0,109215-74-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 20percent DIBAL-H / toluene; hexane / 4 h / -78 °C

2: 80 percent / tetrahydrofuran / 24 h / Heating

3: 96 percent / triethylamine / benzene / 1.) 0 deg C, 5 min, 2.) RT, 15 min, 3.) 55 deg C, 6 h

4: 64 percent / benzene / 24 h / 110 °C / sealed tube

5: 1.) 1.0M borane 2.) 30percent H₂O₂, 2N NaOH / 1.) THF, 0 deg C, 1.5 h, 2.) 0 deg C, 0,5 h

6: 52percent HF / tetrahydrofuran; H₂O / 24 h / Ambient temperature

7: imidazole / dimethylformamide / 48 h / 55 °C

8: 94 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O / 24 h / Ambient temperature

9: tetrahydrofuran / 5 h / Heating

With 1H-imidazole; sodium hydroxide; hydrogen fluoride; borane; dihydrogen peroxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja00251a021

upstream raw materials:

[(3R,4R,4aS,5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl]-carbamic acid benzyl ester

1,1'-Thiocarbonyldiimidazole

((3R,4R,4aS,5S,6S)-5,6-Dihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-carbamic acid benzyl ester

(S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester

Downstream raw materials:

<3aS-(3aα,8α,9α,9aα,9bβ)>-(3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6-oxo-6H-1,3-dioxolo<4,5-f><2>benzopyran-9-yl)carbamic acid phenylmethyl ester

[(3R,4R,4aS,5S,6S,8S,8aS)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl]-carbamic acid benzyl ester

((3aS,5S,5aS,8R,9R,9aS,9bS)-5-Hydroxy-2,2,8-trimethyl-6-oxo-octahydro-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester

N-carbobenzoxy-5,6-O-isopropylidene-5,6,10-triepi-actinobolin