Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester
CAS No.:474409-90-0
Molecular Formula:C₂₆H₂₇N₅O₉S
Molecular Weight:585.594
Hs Code.:

Synonyms:Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

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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 Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Hazard Codes:

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Technology Process of Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-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: 74.0%

: 474409-88-6
Acetic acid (2R,4R,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-3-phenylselanyl-tetrahydro-thiophen-3-yl ester

: 474409-90-0
Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

: Acetic acid (2R,3S,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In toluene; at -70 ℃;
DOI:10.1016/S0040-4039(02)01131-0

Reference yield:

: 209048-61-3
1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol

: 474409-90-0
Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA

1.2: 69 percent / NaBH₄

2.1: 40 percent / acetonitrile; CH₂Cl₂ / -40 °C

3.1: Bu₄NF / tetrahydrofuran

3.2: 90 percent / iPr₂NEt; DMAP / CH₂Cl₂

4.1: m-CPBA / -70 °C

4.2: 96 percent / CH₂Cl₂ / 20 °C

5.1: 46 percent / Bu₃SnH; Et₃B / benzene / 20 °C

With triethyl borane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 4.2: seleno-Pummerer reaction;
DOI:10.1016/S0040-4039(02)01131-0

Reference yield:

: 474409-49-9
1,4-anhydro-1-(tert-butyldimethylsilyloxymethyl)-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-erythropento-1-enitol

: 474409-90-0
Acetic acid (2R,3R,4S,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-(6-benzoylamino-purin-9-yl)-tetrahydro-thiophen-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 40 percent / acetonitrile; CH₂Cl₂ / -40 °C

2.1: Bu₄NF / tetrahydrofuran

2.2: 90 percent / iPr₂NEt; DMAP / CH₂Cl₂

3.1: m-CPBA / -70 °C

3.2: 96 percent / CH₂Cl₂ / 20 °C

4.1: 46 percent / Bu₃SnH; Et₃B / benzene / 20 °C

With triethyl borane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 3.2: seleno-Pummerer reaction;
DOI:10.1016/S0040-4039(02)01131-0