(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

Base Information

Chemical Name:(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide
CAS No.:828935-23-5
Molecular Formula:C₂₃H₂₄ClIN₆O₃
Molecular Weight:594.839
Hs Code.:

Synonyms:(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

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Technology Process of (1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

There total 12 articles about (1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide 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: 60.0%

: 3718-88-5
3-iodobenzylamine hydrochloride

: 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

: 828935-23-5
(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

Guidance literature:: 3-iodobenzylamine hydrochloride; 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; With triethylamine; In methanol; at 20 ℃; for 3h;

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

Reference yield: 46.0%

: 696-40-2
3-iodobenzylamine

: 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

: 828935-23-5
(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

Guidance literature:: With triethylamine; In methanol; at 20 ℃; for 3h;

Reference yield:

: 189996-60-9
2,3-O-isopropylidene-D-erythrose

: 828935-23-5
(1'S,2'R,3'S,4'S,5'S)-4'-[6-(3-iodobenzylamino)-2-chloropurin-9-yl]-2',3'-O-isopropylidene-bicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 60 percent / t-BuOK / tetrahydrofuran / 0 - 20 °C

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

3.1: NaOCl

4.1: tetrahydrofuran / 0 - 30 °C

5.1: 0.293 g / tetrahydrofuran / -78 °C

6.1: 72 percent / NaBH₄ / methanol / 1 h / 20 °C

7.1: 41 percent / TsOH*H₂O / acetone / 8 h / Heating

8.1: 36 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 8 h / 20 °C

9.1: Et₃N / methanol / 3 h / 20 °C

9.2: 60 percent / methanol; H₂O / 6 h / 20 °C

With sodium hypochlorite; sodium tetrahydroborate; oxalyl dichloride; di-isopropyl azodicarboxylate; potassium tert-butylate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetone; 2.1: Swern oxidation / 5.1: Dieckmann condensation / 8.1: Mitsunobu reaction;
DOI:10.1021/jo0487606