(-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

Base Information

Chemical Name:(-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester
CAS No.:808752-80-9
Molecular Formula:C₃₀H₂₈N₆O₅
Molecular Weight:552.59
Hs Code.:

Synonyms:(-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

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Chemical Property of (-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

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Technology Process of (-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

There total 5 articles about (-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl 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: 76.0%

: 808752-66-1
(-)-(3R,5S,8R)-acetic acid 8-allyloxy-7-oxa-[3.3.0]-bicyclooct-1-ene-3-yl ester

: 112233-74-6
N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

: 808752-80-9
(-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

Guidance literature:: N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With 1,2,2,6,6-pentamethylpiperidine; In dimethyl sulfoxide; at 20 ℃; for 0.0833333h;

(-)-(3R,5S,8R)-acetic acid 8-allyloxy-7-oxa-[3.3.0]-bicyclooct-1-ene-3-yl ester; With triisopropyl phosphite; [Pd(dibenzylideneacetone)2]; In tetrahydrofuran; dimethyl sulfoxide; at 70 ℃; for 16h;
DOI:10.1002/chem.200400079

Reference yield:

: 808752-64-9
(-)-(3R,5S,8R)-8-allyloxy-7-oxa-[3.3.0]-bicyclooct-1-ene-3-ol

: 808752-80-9
(-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: pempidine / dimethylsulfoxide / 0.08 h / 20 °C

2.2: 76 percent / P(OiPr)3 / [Pd(dba)2] / dimethylsulfoxide; tetrahydrofuran / 16 h / 70 °C

With 1,2,2,6,6-pentamethylpiperidine; dmap; triethylamine; In dichloromethane; dimethyl sulfoxide;
DOI:10.1002/chem.200400079

Reference yield:

: 8-allyloxy-2-trimethylsilyl-7-oxa-[3.3.0]-bicyclooct-1-ene-3-ol

: 808752-80-9
(-)-(3'R,5'S,8'R)-diphenylcarbamic acid 2-acetylamino-9-(8'-allyloxy-7'-oxa-[3.3.0]-bicyclooct-1'-ene-3'-yl)-9H-purin-6-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: MnO₂ / CH₂Cl₂ / 2 h / 20 °C

1.2: 21 percent / catecholborane; (S)-methyl-oxazaborolidine / toluene; tetrahydrofuran / 3 h / -78 - 20 °C

2.1: 82 percent / aq. t-BuOK / dimethylsulfoxide / 0.5 h / 20 °C

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: pempidine / dimethylsulfoxide / 0.08 h / 20 °C

4.2: 76 percent / P(OiPr)3 / [Pd(dba)2] / dimethylsulfoxide; tetrahydrofuran / 16 h / 70 °C

With 1,2,2,6,6-pentamethylpiperidine; dmap; manganese(IV) oxide; potassium tert-butylate; triethylamine; In dichloromethane; dimethyl sulfoxide;
DOI:10.1002/chem.200400079