((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

Base Information

• Chemical Name: ((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
• CAS No.: 109124-39-2
• Molecular Formula: C₂₁H₂₇NO₇
• Molecular Weight: 405.448

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 15 articles about ((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 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,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)

Guidance literature:

Multi-step reaction with 13 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

11: 85 percent / tri-n-butyltin hydride / benzene / 7 h / Heating

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

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

With 1H-imidazole; sodium hydroxide; Amberlyst 15 acidic resin; boron trifluoride diethyl etherate; hydrogen fluoride; borane; dihydrogen peroxide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/ja00251a021

Reference yield:

N-benzyloxycarbonyl-L-treonine (19728-63-3) → ((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)

Guidance literature:

Multi-step reaction with 14 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

12: 85 percent / tri-n-butyltin hydride / benzene / 7 h / Heating

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

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

With 1H-imidazole; sodium hydroxide; Amberlyst 15 acidic resin; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; borane; dihydrogen peroxide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/ja00251a021

Reference yield:

(2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (104410-78-8) → ((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)

Guidance literature:

Multi-step reaction with 12 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

10: 85 percent / tri-n-butyltin hydride / benzene / 7 h / Heating

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

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

With 1H-imidazole; sodium hydroxide; Amberlyst 15 acidic resin; boron trifluoride diethyl etherate; hydrogen fluoride; borane; dihydrogen peroxide; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/ja00251a021

upstream raw materials:

2-Methoxypropene

((3R,4R,4aS,5S,6S,8S,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester

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

N-benzyloxycarbonyl-L-treonine

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

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

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