pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Base Information

Chemical Name:pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
CAS No.:849611-07-0
Molecular Formula:C₄₀H₄₂Cl₂O₁₃
Molecular Weight:801.672
Hs Code.:

Synonyms:pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

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Chemical Property of pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

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Technology Process of pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

There total 7 articles about pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-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: 69.0%

: 3,5-di-O-chloroacetyl-β-D-arabinofurnose 1,2-(pent-4-enyl orthobenzoate)

: 765274-09-7
pent-4-enyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

: 849611-07-0
pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Guidance literature:: With N-iodo-succinimide; ytterbium(III) triflate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1039/b413694b

Reference yield:

: (2R,3aS,5R,6R,6aS)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

: 849611-07-0
pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N; DMAP / 12 h

2: NaH / dimethylformamide

3: TBDMSOTf

4: 82 percent / TBAF / tetrahydrofuran / 20 °C

5: 69 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; N-iodo-succinimide; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b413694b

Reference yield:

: 765274-01-9
3,5-di-O-benzoyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

: 849611-07-0
pent-4-enyl 5-O-(2-O-benzoyl-3,5-di-O-chloroacetyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / NaOMe / 2 h / 20 °C

2: Et₃N; DMAP / 12 h

3: NaH / dimethylformamide

4: TBDMSOTf

5: 82 percent / TBAF / tetrahydrofuran / 20 °C

6: 69 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; N-iodo-succinimide; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b413694b