methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Base Information

Chemical Name:methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate
CAS No.:883143-21-3
Molecular Formula:C₄₇H₅₁NO₇
Molecular Weight:741.924
Hs Code.:

Synonyms:methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Chemical Property of methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

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Technology Process of methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

There total 3 articles about methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 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:

: 883143-17-7
methyl 2-oxo-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

: 883143-21-3
methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / TiCl₄ / diethyl ether; CH₂Cl₂ / 8 h / 0 - 20 °C

2: 100 percent / NaCNBH₃; AcOH / methanol / 3 h / 0 °C

With titanium tetrachloride; sodium cyanoborohydride; acetic acid; In methanol; diethyl ether; dichloromethane;
DOI:10.1055/s-2005-922768

Reference yield:

: 883143-14-4
((2S,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester

: 883143-21-3
methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 2 h / -78 °C

2: 96 percent / TiCl₄ / diethyl ether; CH₂Cl₂ / 8 h / 0 - 20 °C

3: 100 percent / NaCNBH₃; AcOH / methanol / 3 h / 0 °C

With titanium tetrachloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In methanol; diethyl ether; dichloromethane;
DOI:10.1055/s-2005-922768

Reference yield:

: 883143-13-3
((2R,3R,4S,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-trimethylsilanyloxy-acetic acid methyl ester

: 883143-21-3
methyl (2S)-benzylamino-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / aq. TFA / tetrahydrofuran / 20 °C

2: 80 percent / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 2 h / -78 °C

3: 96 percent / TiCl₄ / diethyl ether; CH₂Cl₂ / 8 h / 0 - 20 °C

4: 100 percent / NaCNBH₃; AcOH / methanol / 3 h / 0 °C

With titanium tetrachloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1055/s-2005-922768