<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

Base Information

• Chemical Name: <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
• CAS No.: 104410-84-6
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368

Synonyms:<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

Chemical Property of <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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of <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

There total 11 articles about <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 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%

(4R,5R,6R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (104427-25-0) → <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)

Guidance literature:

With hydrogen fluoride; water; In tetrahydrofuran;

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

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:

(R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104486-64-8) → <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)

Guidance literature:

Multistep reaction;

DOI:10.1039/c39860001350

upstream raw materials:

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

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

<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

<4R-<4α,5β,6α(1R*,2R*)>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<<(phenylmethoxy)carbonyl>amino>propyl>-5-hydroxy-1-cyclohexene-1-carboxylic acid methyl ester

Downstream raw materials:

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

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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