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

Base Information

• Chemical Name: ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester
• CAS No.: 109124-44-9
• Molecular Formula: C₁₈H₂₃NO₇
• Molecular Weight: 365.383

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

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

There total 13 articles about ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-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: 50.0%

<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) → ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester (109124-44-9)

Guidance literature:

With sodium acetate; zinc; In acetic acid;

DOI:10.1039/c39860001350

Reference yield: 33.0%

<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) → <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) + ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester (109124-44-9)

Guidance literature:

With sodium acetate; zinc; In acetic acid; for 0.5h; Ambient temperature;

DOI:10.1021/ja00251a021

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester (109124-44-9)

Guidance literature:

Multi-step reaction with 9 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

9: 50 percent / activated zinc dust, sodium acetate / acetic acid / 0.5 h / Ambient temperature

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

DOI:10.1021/ja00251a021

upstream raw materials:

<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

(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:

C₂₇H₃₄N₂O₈

<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

C₂₄H₃₁NO₇

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