((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

Base Information

• Chemical Name: ((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
• CAS No.: 104421-37-6
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368
• Mol file: 104421-37-6.mol

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 9 articles about ((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 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: 99.0%

(4S,5S,6S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (104486-65-9) → ((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)

Guidance literature:

With hydrogen fluoride; water; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)84109-X

Reference yield:

(S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104410-81-3) → ((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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 52percent HF / tetrahydrofuran; H₂O / 24 h / Ambient temperature

With sodium hydroxide; hydrogen fluoride; borane; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1021/ja00251a021

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → ((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)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; sodium hydroxide; hydrogen fluoride; borane; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00251a021

upstream raw materials:

(4S,5S,6S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

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

N-benzyloxycarbonyl-L-treonine

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

Downstream 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

<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

((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