1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose
• CAS No.: 449763-01-3
• Molecular Formula: C₃₆H₅₃NO₈Si₂
• Molecular Weight: 683.99
• Mol file: 449763-01-3.mol

Synonyms:

Chemical Property of 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose

There total 5 articles about 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose 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:

(2S,3R)-2,3-Bis-benzyloxy-N-[(1R,2S,3S,4R,5R)-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl]-succinamic acid → 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose (449763-01-3)

Guidance literature:

With acetic anhydride; In pyridine; at 20 ℃; for 24h;

DOI:10.1007/s007060200023

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose (449763-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / pyridine / 20 h / 20 °C

2: 95 percent / H₂ / 10 percent Pd/C / ethyl acetate; methanol / 24 h / 20 °C

3: N-ethyldiisopropylamine / CH₂Cl₂ / 20 h / 20 °C

4: 939 mg / acetic anhydride / pyridine / 24 h / 20 °C

With hydrogen; acetic anhydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane; ethyl acetate;

DOI:10.1007/s007060200023

Reference yield:

1,6-anhydro-3-azido-3-deoxy-β-D-glucopyranose (94614-37-6) → 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-((3'R,4'R)-3',4'-bis-O-benzyl)-tartarimido-β-D-glucopyranose (449763-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / pyridine / 20 h / 20 °C

2: 95 percent / H₂ / 10 percent Pd/C / ethyl acetate; methanol / 24 h / 20 °C

3: N-ethyldiisopropylamine / CH₂Cl₂ / 20 h / 20 °C

4: 939 mg / acetic anhydride / pyridine / 24 h / 20 °C

With hydrogen; acetic anhydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In pyridine; methanol; dichloromethane; ethyl acetate;

DOI:10.1007/s007060200023

upstream raw materials:

t-butyldimethylsiyl triflate

1,6-anhydro-3-azido-3-deoxy-β-D-glucopyranose

3-amino-1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-glucopyranose

1,6-anhydro-3-azido-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-glucopyranose