3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine
• CAS No.: 141599-08-8
• Molecular Formula: C₃₄H₄₃NO₅Si
• Molecular Weight: 573.805
• Mol file: 141599-08-8.mol

Synonyms:3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine

Chemical Property of 3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine

There total 1 articles about 3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine 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: 86.0%

3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam (121250-72-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine (141599-08-8)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90975-5

Reference yield:

3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine (141599-08-8) → E 2-diphenylmethoxcarbonylvinyl-1'-diphenylmethoxycarbonylvinyl ether (141599-20-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

2: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, room temperature, 2) H₂O

3: diethyl ether

4: 69 percent / PPh₃, CBr₄, pyridine / 0.67 h / 0 °C

5: 33 percent / CsF / acetonitrile / 16 h / Ambient temperature

With pyridine; sodium chlorite; sodium periodate; carbon tetrabromide; hydrogen; dihydrogen peroxide; triphenylphosphine; cesium fluoride; palladium on activated charcoal; In diethyl ether; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)90975-5

Reference yield:

3,4,6-tri-O-benzyl-N-t-butyldimethylsilyl-2-C:1-N-carbonyl-2-deoxy-α-D-galactopyranosylamine (141599-08-8) → Z and E 1-amino-2-diphenylmethoxycarbonyl-2-(1'-diphenylmethoxycarbonyl)vinyloxycarbonyl-ethylene (141599-23-7,141599-24-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

2: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, room temperature, 2) H₂O

3: diethyl ether

4: 69 percent / PPh₃, CBr₄, pyridine / 0.67 h / 0 °C

5: 16 percent / CsF / acetonitrile / 16 h / Ambient temperature

With pyridine; sodium chlorite; sodium periodate; carbon tetrabromide; hydrogen; dihydrogen peroxide; triphenylphosphine; cesium fluoride; palladium on activated charcoal; In diethyl ether; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)90975-5

upstream raw materials:

3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

tert-butyldimethylsilyl chloride

Downstream raw materials:

E 2-diphenylmethoxcarbonylvinyl-1'-diphenylmethoxycarbonylvinyl ether

Z and E 1-amino-2-diphenylmethoxycarbonyl-2-(1'-diphenylmethoxycarbonyl)vinyloxycarbonyl-ethylene

(3S,4S) 3-diphenylmethoxycarbonyl-4-(1'-diphenylmethoxycarbonyl)vinyloxy-azetidinone-2

(1S,3R,5S) 7-aza-3,5-di-(diphenylmethoxycarbonyl)-2-oxabicyclo<3.2.0>heptan-7-one