<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

Base Information

• Chemical Name: <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
• CAS No.: 104410-89-1
• Molecular Formula: C₂₁H₂₅NO₇
• Molecular Weight: 403.432
• Mol file: 104410-89-1.mol

Synonyms:<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

Chemical Property of <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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <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

There total 17 articles about <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 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%

((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 (109124-39-2) → <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 (104410-89-1)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/ja00251a021

Reference yield:

[(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 (104410-87-9) → <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 (104410-89-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O / 24 h / Ambient temperature

2: tetrahydrofuran / 5 h / Heating

3: 85 percent / tri-n-butyltin hydride / benzene / 7 h / Heating

4: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

5: Amberlyst 15 acidic resin / tetrahydrofuran / 6 h / Ambient temperature

6: 81 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

With Amberlyst 15 acidic resin; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium acetate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1021/ja00251a021

Reference yield:

((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 (104421-37-6) → <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 (104410-89-1)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 94 percent / N-methylmorpholine-N-oxide / osmium tetroxide / acetone; H₂O / 24 h / Ambient temperature

3: tetrahydrofuran / 5 h / Heating

4: 85 percent / tri-n-butyltin hydride / benzene / 7 h / Heating

5: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

6: Amberlyst 15 acidic resin / tetrahydrofuran / 6 h / Ambient temperature

7: 81 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; Amberlyst 15 acidic resin; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium acetate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1021/ja00251a021

upstream raw materials:

2-Methoxypropene

[(3aR,5S,6S,6aS,7R,8R,10aS)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-methyl-10-oxo-2-thioxo-hexahydro-[1,3]dioxolo[4,5-i]isochromen-7-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

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

Downstream raw materials:

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