<1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester

Base Information

• Chemical Name: <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester
• CAS No.: 109124-43-8
• Molecular Formula: C₁₈H₂₁NO₇
• Molecular Weight: 363.367

Synonyms:<1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester

Chemical Property of <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester

There total 11 articles about <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-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: 42.0%

<3R-(3α,4α,4aβ,5β,6α)>-(3,4,4a,5,6,7-hexahydro-5,6-dihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)carbamic acid phenylmethyl ester (104410-84-6) → <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester (109124-43-8)

Guidance literature:

With disodium hydrogenphosphate; 3,5-dinitrobenzoperoxoic acid; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00251a021

Reference yield: 42.0%

(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) → <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester (109124-43-8)

Guidance literature:

With disodium hydrogenphosphate; 3,5-dinitrobenzoperoxoic acid;

DOI:10.1039/c39860001350

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester (109124-43-8)

Guidance literature:

Multi-step reaction with 8 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: 21 percent / benzene / 24 h / 110 °C / sealed tube

6: 1.) 1.0M borane, 2.) 30percent H₂O₂, 2N NaOH / 1.) THF, 0 deg C, 1 h, 2.) H₂O, 0 deg C, 0.5 h

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

8: 42 percent / 3,5-dinitroperoxybenzoic acid, Na₂HPO₄ / CH₂Cl₂ / 24 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; disodium hydrogenphosphate; 3,5-dinitrobenzoperoxoic acid; hydrogen fluoride; borane; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00251a021

upstream raw materials:

<3R-(3α,4α,4aβ,5β,6α)>-(3,4,4a,5,6,7-hexahydro-5,6-dihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)carbamic acid phenylmethyl 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

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

N-benzyloxycarbonyl-L-treonine

Downstream raw materials:

<3R-(3α,4α,4aβ,5β,6α)>-(3,4,4a,5,6,7-hexahydro-5,6-dihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)carbamic acid phenylmethyl ester

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

C₂₄H₃₁NO₇

<3'aR-(3'aα,8'β,9'β,9'aα,9'bβ)>-(3'a,4',8',9',9'a,9'b-hexahydro-5'-hydroxy-8'-methyl-6'-oxospirodioxolo<4,5f><2>benzopyran>-9'-yl)carbamic acid phenylmethyl ester

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