4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

Base Information

Chemical Name:4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside
CAS No.:189382-68-1
Molecular Formula:C₂₆H₂₁NO₄S₂
Molecular Weight:475.589
Hs Code.:

Synonyms:4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

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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 4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

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Technology Process of 4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

There total 5 articles about 4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside 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: 91.0%

: 36801-01-1
4-cyanobenzenethiol

: 189382-65-8
1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol

: 189382-68-1
4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

Guidance literature:: 1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol; With hydrogen bromide; In toluene; at 10 ℃; for 0.333333h;

With silver(I) acetate; In toluene; acetonitrile; at 20 ℃; for 2h;

4-cyanobenzenethiol; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; acetonitrile; at -10 - 20 ℃; for 1h;
DOI:10.1016/S0008-6215(97)00001-3

Reference yield: 11.0%

: 61628-44-2
sodium 4-cyanobenzenethiolate

: 189382-65-8
1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol

: 4-cyanophenyl 4-O-benzoyl-1,5-dithio-D-glycero-pent-2-enopyranoside

: 189382-68-1
4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

Guidance literature:: 1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol; With hydrogen bromide; In toluene; at 10 ℃; for 0.333333h;

sodium 4-cyanobenzenethiolate; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 24h;
DOI:10.1016/S0008-6215(97)00001-3

Reference yield:

: 38768-95-5
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide

: 189382-68-1
4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / 4-picoline; Zn / toluene / 1 h / 80 °C

2.1: MeOH; NaOMe / 1 h / 20 °C

3.1: 4.95 g / pyridine / CH₂Cl₂ / 20 °C

4.1: HBr / toluene / 0.33 h / 10 °C

4.2: silver acetate / toluene; acetonitrile / 2 h / 20 °C

4.3: 91 percent / trimethylsilyl triflate / toluene; acetonitrile; CH₂Cl₂ / 1 h / -10 - 20 °C

With pyridine; picoline; methanol; hydrogen bromide; sodium methylate; zinc; In dichloromethane; toluene; 1.1: Reduction / 2.1: Zemplen deacetylation / 3.1: benzoylation / 4.1: Addition / 4.2: Substitution / 4.3: Condensation;
DOI:10.1016/S0008-6215(97)00001-3