2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Base Information

Chemical Name:2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol
CAS No.:544686-91-1
Molecular Formula:C₄₈H₅₇NO₈Si
Molecular Weight:804.068
Hs Code.:

Synonyms:2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

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Chemical Property of 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

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Technology Process of 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

There total 10 articles about 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol 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:

: (2R,3S,4R,5R,6S)-6-[(S)-1-Allyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-5-azido-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: 544686-91-1
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 5 steps

1: 8.17 g / sodium hydride / dimethylformamide / 24 h / 20 °C

2: 1,3-propanedithiol; Et₃N / pyridine; H₂O

3: 5.82 g / pyridine / 2 h

4: DBU / (Ph₃P)3RhCl / ethanol / 0.25 h / 90 °C

5: 1.98 g / aqueous HCl / acetone / 0.25 h / 70 °C

With pyridine; 1.3-propanedithiol; hydrogenchloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Wilkinson's catalyst; In pyridine; ethanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tetasy.2004.11.070

Reference yield:

: 544686-89-7
3-O-allyl-2-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

: 544686-91-1
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 4 steps

1: 1,3-propanedithiol; Et₃N / pyridine; H₂O

2: 5.82 g / pyridine / 2 h

3: DBU / (Ph₃P)3RhCl / ethanol / 0.25 h / 90 °C

4: 1.98 g / aqueous HCl / acetone / 0.25 h / 70 °C

With pyridine; 1.3-propanedithiol; hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Wilkinson's catalyst; In pyridine; ethanol; water; acetone;
DOI:10.1016/j.tetasy.2004.11.070

Reference yield:

: (2S,3R,4R,5S,6R)-2-[(S)-1-Allyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ylamine

: 544686-91-1
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 3 steps

1: 5.82 g / pyridine / 2 h

2: DBU / (Ph₃P)3RhCl / ethanol / 0.25 h / 90 °C

3: 1.98 g / aqueous HCl / acetone / 0.25 h / 70 °C

With pyridine; hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; Wilkinson's catalyst; In ethanol; acetone;
DOI:10.1016/j.tetasy.2004.11.070