2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Base Information

Chemical Name:2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
CAS No.:849611-14-9
Molecular Formula:C₂₉H₃₁NO₈
Molecular Weight:521.567
Hs Code.:

Synonyms:2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

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Chemical Property of 2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

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Technology Process of 2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

There total 7 articles about 2-(N-benzyloxycarbonyl)aminoethyl 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: 74.0%

: 849611-26-3
Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-2-(2-benzyloxycarbonylamino-ethoxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

: 849611-14-9
2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 6h;
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

: 849611-14-9
2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N; DMAP / 12 h

2: NaH / dimethylformamide

3: 82 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 0 °C

4: 74 percent / TBAF; HOAc / tetrahydrofuran / 6 h

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

Reference yield:

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

: 849611-14-9
2-(N-benzyloxycarbonyl)aminoethyl 2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: NaH / dimethylformamide

2: 82 percent / N-iodosuccinimide; Yb(OTf)3 / CH₂Cl₂ / 0.5 h / 0 °C

3: 74 percent / TBAF; HOAc / tetrahydrofuran / 6 h

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