2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-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)-3-O-allyl-1-O-tert-butyldiphenylsilyl-sn-glycerol
CAS No.:544686-90-0
Molecular Formula:C₅₁H₆₁NO₈Si
Molecular Weight:844.133
Hs Code.:

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

There total 12 articles about 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-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: 83.0%

: 507-09-5
tiolacetic acid

: 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

: 544686-90-0
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: at 40 ℃;
DOI:10.1016/j.tetasy.2004.11.070

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

: 544686-90-0
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 3 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

With pyridine; 1.3-propanedithiol; sodium hydride; triethylamine; In pyridine; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2004.11.070

Reference yield:

: 544686-87-5
(S)-(-)-1-allyl-3-tert-butyldiphenylsilyl-sn-glycerol

: 544686-90-0
2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-allyl-1-O-tert-butyldiphenylsilyl-sn-glycerol

Guidance literature:: Multi-step reaction with 5 steps

1: TMSOTf / CH₂Cl₂ / 0.03 h / 20 °C

2: MeOH; NaOMe / pH 9

3: 8.17 g / sodium hydride / dimethylformamide / 24 h / 20 °C

4: 1,3-propanedithiol; Et₃N / pyridine; H₂O

5: 5.82 g / pyridine / 2 h

With pyridine; 1.3-propanedithiol; methanol; sodium methylate; sodium hydride; triethylamine; trimethylsilyl trifluoromethanesulfonate; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2004.11.070