n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

Base Information

Chemical Name:n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside
CAS No.:920267-70-5
Molecular Formula:C₂₈H₃₈O₅
Molecular Weight:454.607
Hs Code.:

Synonyms:n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

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Chemical Property of n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

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Technology Process of n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

There total 10 articles about n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside 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: 82.0%

: 2,3-anhydro-5,6-di-O-benzyl-β-D-gulofuranosyl-p-tolyl-(R/S)-sulfoxide

: 111-87-5
octanol

: 920267-70-5
n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

Guidance literature:: 2,3-anhydro-5,6-di-O-benzyl-β-D-gulofuranosyl-p-tolyl-(R/S)-sulfoxide; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; In dichloromethane; at -78 - -40 ℃;

octanol; In dichloromethane; at -40 ℃;
DOI:10.1021/jo061713o

Reference yield:

: 920267-51-2
p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

: 111-87-5
octanol

: n-octyl 2,3-anhydro-5,6-di-O-benzyl-β-D-gulofuranoside

: 920267-70-5
n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

Guidance literature:: With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -40 - -25 ℃;
DOI:10.1021/jo061713o

Reference yield:

: 920267-59-0
p-tolyl 2,3-anhydro-1-thio-β-D-gulofuranoside

: 920267-70-5
n-octyl 2,3-anhydro-5,6-di-O-benzyl-α-D-gulofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0.08 h / 0 °C

1.2: 93 percent / dimethylformamide; various solvent(s) / 6 h / 20 °C

2.1: 58 percent / m-CPBA / CH₂Cl₂ / -78 - 20 °C

3.1: 2,6-di-tert-butyl-4-methylpyridine; Tf₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / -78 - -40 °C

3.2: 82 percent / CH₂Cl₂ / -40 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo061713o