N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester
• CAS No.: 114117-10-1
• Molecular Formula: C₆₀H₆₆N₂O₁₅
• Molecular Weight: 1055.19

Synonyms:N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester

Chemical Property of N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester

There total 10 articles about N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester 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:

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) → N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester (114117-10-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / TMSOTf / CH₂Cl₂ / 2 h

2: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: NiCl₂*6H₂O, boric acid, sodium borohydride / CH₂Cl₂; ethanol / Ambient temperature

4: 1.00 g / CH₂Cl₂ / 10 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; boric acid; trifluoroacetic acid; nickel dichloride; In ethanol; dichloromethane;

DOI:10.1016/0008-6215(87)80135-0

Reference yield:

tert-butyldimethylsilyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-galactopyranoside (114117-04-3) → N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester (114117-10-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 10.7 percent / diethyl ether-boron trifluoride / CH₂Cl₂; hexane / 6 h

2: 92 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 3 h / -5 °C

3: 95 percent / 1.) potassium carbonate, 2.) sodium hydride / CH₂Cl₂ / 1.) 6 h, 2.) 2 h

4: 53 percent / TMSOTf / CH₂Cl₂ / 2 h

5: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: NiCl₂*6H₂O, boric acid, sodium borohydride / CH₂Cl₂; ethanol / Ambient temperature

7: 1.00 g / CH₂Cl₂ / 10 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; boric acid; sodium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; nickel dichloride; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1016/0008-6215(87)80135-0

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (90358-01-3) → N-benzyloxycarbonyl-3-O-<2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-L-serine benzyl ester (114117-10-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 10.7 percent / diethyl ether-boron trifluoride / CH₂Cl₂; hexane / 6 h

2: 92 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 3 h / -5 °C

3: 95 percent / 1.) potassium carbonate, 2.) sodium hydride / CH₂Cl₂ / 1.) 6 h, 2.) 2 h

4: 53 percent / TMSOTf / CH₂Cl₂ / 2 h

5: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: NiCl₂*6H₂O, boric acid, sodium borohydride / CH₂Cl₂; ethanol / Ambient temperature

7: 1.00 g / CH₂Cl₂ / 10 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; boric acid; sodium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; nickel dichloride; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1016/0008-6215(87)80135-0

upstream raw materials:

acetic anhydride

N-benzyloxycarbonyl-L-serine benzyl ester

tert-butyldimethylsilyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-galactopyranoside

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

Downstream raw materials:

3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine

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