{9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

Base Information

Chemical Name:{9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester
CAS No.:111189-94-7
Molecular Formula:C₂₂H₂₄N₆O₈S
Molecular Weight:532.534
Hs Code.:

{9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

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Chemical Property of {9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

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Technology Process of {9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

There total 14 articles about {9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl 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:

: 7129-41-1,54460-11-6
6-oxabicyclo<3.1.0>hex-2-ene

: 111189-94-7,111265-80-6,111265-82-8,111265-83-9
{9-[(3aR,4S,6R,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 67 percent / <(i-C₃H₇O)3P>4Pd / tetrahydrofuran; dimethylsulfoxide / 1.) 0 deg C for 3 h 2.) 25 deg C overnight

2: 85 percent / piridine / CH₂Cl₂ / from 0 deg C to room temperature

3: 82 percent / Ph₃P / (dba)3Pd₂(CHCl₃) / tetrahydrofuran / Heating

4: KMnO₄, 0.6percent aq. NaOH / H₂O / 0 °C

5: TsOH / acetone / 50 °C

With pyridine; sodium hydroxide; potassium permanganate; toluene-4-sulfonic acid; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; C₃₆H₈₄O₁₂P₄Pd; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/ja00210a064

Reference yield:

: 7129-41-1,54460-11-6
6-oxabicyclo<3.1.0>hex-2-ene

: 111189-94-7,111265-80-6,111265-82-8,111265-83-9
{9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 67 percent / <(i-C₃H₇O)3P>4Pd / tetrahydrofuran; dimethylsulfoxide / 1.) 0 deg C for 3 h 2.) 25 deg C overnight

2: 85 percent / piridine / CH₂Cl₂ / from 0 deg C to room temperature

3: 82 percent / Ph₃P / (dba)3Pd₂(CHCl₃) / tetrahydrofuran / Heating

4: osmium tetroxide, N-methyl-morpholine N-oxide / tetrahydrofuran; H₂O

5: TsOH / acetone / 50 °C

With pyridine; osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; C₃₆H₈₄O₁₂P₄Pd; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/ja00210a064

Reference yield:

: 74738-03-7
<(phenylsulfonyl)nitromethyl>lithium

: 111189-94-7,111265-80-6,111265-82-8,111265-83-9
{9-[(3aR,4S,6R,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / Ph₃P / (dba)3Pd₂(CHCl₃) / tetrahydrofuran / Heating

2: KMnO₄, 0.6percent aq. NaOH / H₂O / 0 °C

3: TsOH / acetone / 50 °C

With sodium hydroxide; potassium permanganate; toluene-4-sulfonic acid; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; water; acetone;
DOI:10.1021/ja00210a064