(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

Base Information

Chemical Name:(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester
CAS No.:378238-84-7
Molecular Formula:C₃₃H₃₃N₅O₉S
Molecular Weight:675.719
Hs Code.:

(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

Synonyms:(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

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Chemical Property of (2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

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Technology Process of (2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

There total 12 articles about (2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl 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: 75.0%

: 4005-49-6
N-benzoyladenine

: 378238-83-6
(2S,3S,3aR,6R,6aS)-5,6-Diacetoxy-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

: 378238-84-7
(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

Guidance literature:: N-benzoyladenine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 80 ℃; for 0.5h;

(2S,3S,3aR,6R,6aS)-5,6-Diacetoxy-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 80 ℃; for 1.5h; Further stages.;
DOI:10.1021/ol0167210

Reference yield:

: 108-98-5
thiophenol

: 378238-84-7
(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 30 percent / AIBN; NaHCO₃ / CHCl₃ / 36 h / Heating

2.1: H₂SO₄ / acetic acid; CH₂Cl₂ / 7 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / 80 °C

3.2: 75 percent / Me₃SiOTf / acetonitrile / 1.5 h / 80 °C

With N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium hydrogencarbonate; In dichloromethane; chloroform; acetic acid; acetonitrile;
DOI:10.1021/ol0167210

Reference yield:

: 762-21-0
acetylenedicarboxylic acid diethyl ester

: 378238-84-7
(2S,3S,3aR,5R,6R,6aS)-6-Acetoxy-5-(6-benzoylamino-purin-9-yl)-2-ethoxycarbonylmethyl-3-phenylsulfanyl-hexahydro-furo[3,2-b]furan-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiN(SiMe₃)2 / diethyl ether / 0.25 h / -78 °C

1.2: 86 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 33 percent / n-Bu₃SnH; AIBN / benzene / 6 h / 80 °C

3.1: 30 percent / AIBN; NaHCO₃ / CHCl₃ / 36 h / Heating

4.1: H₂SO₄ / acetic acid; CH₂Cl₂ / 7 h / 20 °C

5.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / 80 °C

5.2: 75 percent / Me₃SiOTf / acetonitrile / 1.5 h / 80 °C

With N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; In diethyl ether; dichloromethane; chloroform; acetic acid; acetonitrile; benzene;
DOI:10.1021/ol0167210