(1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

Base Information

Chemical Name:(1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide
CAS No.:828935-24-6
Molecular Formula:C₂₅H₂₇ClN₆O₃
Molecular Weight:494.981
Hs Code.:

Synonyms:(1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

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Chemical Property of (1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

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Technology Process of (1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

There total 11 articles about (1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide 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: 48.0%

: 74-89-5
methylamine

: 793695-60-0
ethyl (1'S,2'R,3'S,4'R,5'S)-4'-(2,6-dichloropurin-9-yl)-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexane-1'-carboxylate

: (±)-trans-2-phenyl-cyclopropylaminehydrochloride

: 828935-24-6
(1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

Guidance literature:: ethyl (1'S,2'R,3'S,4'R,5'S)-4'-(2,6-dichloropurin-9-yl)-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexane-1'-carboxylate; (±)-trans-2-phenyl-cyclopropylaminehydrochloride; With triethylamine; In methanol; at 20 ℃; for 3h;

methylamine; In methanol; water; at 20 ℃; for 6h;
DOI:10.1021/jo0487606

Reference yield: 48.0%

: 828935-24-6
(1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

Guidance literature:

Reference yield:

: 25581-41-3
D-erythronolactone acetonide

: 828935-24-6
(1'S,2'R,3'S,4'R,5'S)-(4'-{2-chloro-6-[(trans-2-phenylcyclopropyl)amino]purin-9-yl}-2',3'-O-(isopropylidene)bicyclo[3.1.0]hexyl)-N-methylcarboxamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 90 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2.1: 60 percent / t-BuOK / tetrahydrofuran / 0 - 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: NaOCl

5.1: tetrahydrofuran / 0 - 30 °C

6.1: 0.293 g / tetrahydrofuran / -78 °C

7.1: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

8.1: 41 percent / TsOH*H₂O / acetone / 8 h / Heating

9.1: 36 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 8 h / 20 °C

10.1: Et₃N / methanol / 3 h / 20 °C

10.2: 48 percent / methanol; H₂O / 6 h / 20 °C

With sodium hypochlorite; sodium tetrahydroborate; oxalyl dichloride; di-isopropyl azodicarboxylate; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetone; 3.1: Swern oxidation / 6.1: Dieckmann condensation / 9.1: Mitsunobu reaction;
DOI:10.1021/jo0487606