(3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester
• CAS No.: 378238-82-5
• Molecular Formula: C₂₂H₂₈O₈S
• Molecular Weight: 452.526
• Mol file: 378238-82-5.mol

Synonyms:

Chemical Property of (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester

There total 8 articles about (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-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: 30.0%

thiophenol (108-98-5) + (3aR,3bS,5R,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-3a,3b,5,7a-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester (378238-81-4) → (3aR,3bS,5S,6R,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester + (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester (378238-82-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); sodium hydrogencarbonate; In chloroform; for 36h; Heating;

DOI:10.1021/ol0167210

Reference yield:

acetylenedicarboxylic acid diethyl ester (762-21-0) → (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester (378238-82-5)

Guidance literature:

Multi-step reaction with 3 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

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; In diethyl ether; chloroform; benzene;

DOI:10.1021/ol0167210

Reference yield:

(3aR,6S,6aR)-5-[1-Iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (378238-91-6) → (3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester (378238-82-5)

Guidance literature:

Multi-step reaction with 3 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

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; In diethyl ether; chloroform; benzene;

DOI:10.1021/ol0167210

upstream raw materials:

thiophenol

(3aR,3bS,5R,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-3a,3b,5,7a-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester

acetylenedicarboxylic acid diethyl ester

(3aR,6S,6aR)-5-[1-Iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

(2R,5R,6R,6aS)-5-(6-Benzoylamino-purin-9-yl)-2-carboxymethyl-6-hydroxy-2,5,6,6a-tetrahydro-furo[3,2-b]furan-2-carboxylic acid

N⁶-benzoyladenine

(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

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