ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

Base Information

Chemical Name:ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside
CAS No.:1263058-33-8
Molecular Formula:C₃₀H₃₂Cl₂O₁₂S
Molecular Weight:687.549
Hs Code.:

Synonyms:ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

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Chemical Property of ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

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Technology Process of ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

There total 3 articles about ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside 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%

: 1263058-11-2
3-O-chloroacetyl-β-D-arabinofuranose 1,2,5-orthobenzoate

: 75-08-1
ethanethiol

: 1263058-23-6
ethyl 2-O-benzoyl-3-O-chloroacetyl-1-thio-α-D-arabinofuranoside

: 1263058-33-8
ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -25 ℃; Molecular sieve;
DOI:10.1016/j.carres.2010.11.002

Reference yield:

: 7473-42-9,22861-07-0,38837-17-1,42793-97-5,52783-53-6,52783-87-6,69350-76-1,69927-20-4,84518-41-2,103238-80-8,105309-18-0,109959-28-6,109959-29-7,114923-83-0,120964-98-9
methyl tri-O-benzoyl-α-D-arabinofuranoside

: 1263058-23-6
ethyl 2-O-benzoyl-3-O-chloroacetyl-1-thio-α-D-arabinofuranoside

: 1263058-33-8
ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: Dichloromethyl methyl ether; tin(IV) chloride / dichloromethane

2: tetrabutylammomium bromide; triethylamine / methanol; dichloromethane / Molecular sieve

3: sodium methylate / methanol / 16 h / 20 °C

4: 2,4,6-trimethyl-pyridine / dichloromethane / 0.5 h / Cooling with ice

5: tin(IV) chloride / dichloromethane / -25 °C / Molecular sieve

With 2,4,6-trimethyl-pyridine; Dichloromethyl methyl ether; tetrabutylammomium bromide; sodium methylate; tin(IV) chloride; triethylamine; In methanol; dichloromethane;
DOI:10.1016/j.carres.2010.11.002

Reference yield:

: 282107-49-7
β-D-arabinofuranose 1,2,5-orthobenzoate

: 1263058-23-6
ethyl 2-O-benzoyl-3-O-chloroacetyl-1-thio-α-D-arabinofuranoside

: 1263058-33-8
ethyl 5-O-(3-O-chloroacetyl-2-O-benzoyl-α-D-arabinofuranosyl)-3-O-chloroacetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 2,4,6-trimethyl-pyridine / dichloromethane / 0.5 h / Cooling with ice

2: tin(IV) chloride / dichloromethane / -25 °C / Molecular sieve

With 2,4,6-trimethyl-pyridine; tin(IV) chloride; In dichloromethane;
DOI:10.1016/j.carres.2010.11.002