tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside
CAS No.:688315-49-3
Molecular Formula:C₃₃H₄₇N₃O₁₅Si
Molecular Weight:753.833
Hs Code.:

Synonyms:tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

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Chemical Property of tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

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Technology Process of tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

There total 17 articles about tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside 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: 98.0%

: 688315-52-8
benzoic acid 4,5-diacetoxy-2-[3-acetoxy-5-azido-2-{[tert-butoxycarbonyl-(1-ethyl-propyl)-amino]-acetoxymethyl}-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-4-yloxy]-6-acetoxymethyl-tetrahydro-pyran-3-yl ester

: 688315-49-3
tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

Guidance literature:: benzoic acid 4,5-diacetoxy-2-[3-acetoxy-5-azido-2-{[tert-butoxycarbonyl-(1-ethyl-propyl)-amino]-acetoxymethyl}-6-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-4-yloxy]-6-acetoxymethyl-tetrahydro-pyran-3-yl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

With 4-methyl-morpholine; S-phenyl thioacetate; at 20 ℃; for 0.5h; pH=8 - 9; Further stages.;
DOI:10.1016/j.tetlet.2004.02.032

Reference yield:

: Benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-((2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-{2-[1-(1-ethyl-propyl)-3-phenyl-thioureido]-acetoxymethyl}-tetrahydro-pyran-4-yloxy)-6-acetoxymethyl-tetrahydro-pyran-3-yl ester

: 688315-49-3
tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1002/ejoc.200500382

Reference yield:

: 1053380-79-2
{(1-Ethyl-propyl)-[2-(1-ethyl-propylamino)-acetyl]-amino}-acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-5-azido-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

: 688315-49-3
tert-butyldimethylsilyl O-(3,4,6-tri-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 114 mg / aq. NaHCO₃ / 0.5 h / 20 °C

2: 89 percent / NIS; TfOH / CH₂Cl₂ / 2 h / -40 °C

3: TFA / CH₂Cl₂ / 0.5 h / 20 °C

4: NMM / dimethylformamide / 0.5 h / 20 °C

5: TFA / CH₂Cl₂ / 0.5 h / 20 °C

6: 83 mg / aq. NaHCO₃ / 0.5 h / 20 °C

7: 99 percent / pyridine / 2 h / 20 °C

8: TFA / CH₂Cl₂ / 0.5 h / 20 °C

9: NMM / dimethylformamide / 0.5 h / 20 °C

10: 33 mg / TFA / CH₂Cl₂ / 0.5 h / 20 °C

With 4-methyl-morpholine; pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200500382