2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside
• CAS No.: 409098-29-9
• Molecular Formula: C₃₈H₆₁N₃O₂₀
• Molecular Weight: 879.91

Synonyms:2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside

Chemical Property of 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside

There total 16 articles about 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside 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: 56.0%

2-aminoethyl α-L-fucopyranoside (153252-87-0) + 2-(tert-butyloxycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-mannosyloxy)methyl]benzoyl}(2-propanoyl)amino]-β-D-glucopyranoside (409098-28-8) → 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside (409098-29-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 45 ℃; for 12h;

DOI:10.1002/1099-0690(20021)2002:1<79::AID-EJOC79>3.0.CO;2-1

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside (409098-29-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 3.80 g / ethyl acetate / 20 °C

2: 96 percent / NaOMe / methanol / 1 h / 20 °C

3: 64 percent / pyridine / 0 - 20 °C

4: 97 percent / pyridine / 12 h / 4 °C

5: 72 percent / NaN₃ / dimethylformamide / 24 h / 80 °C

6: 98 percent / NaOMe / methanol / 1 h / 20 °C

7: H₂ / 10 percent Pd-C / methanol / 10 h / 20 °C

8: 0.60 g / methanol / 18 h / 40 °C

9: 79 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; i-Pr₂NEt / dimethylformamide / 6 h / 45 °C

10: 100 percent / LiOH*H₂O / methanol; H₂O / 12 h / 0 °C

11: 56 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; i-Pr₂NEt / dimethylformamide / 12 h / 45 °C

With pyridine; lithium hydroxide; sodium azide; hydrogen; sodium methylate; N-ethyl-N,N-diisopropylamine; HATU; palladium on activated charcoal; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; 8: Michael addition;

DOI:10.1002/1099-0690(20021)2002:1<79::AID-EJOC79>3.0.CO;2-1

Reference yield:

2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (139888-80-5) → 2-(tert-butylycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-manno-carbamoyl)syloxy]methyl}benzoyl](2-{[2-(α-L-fucosyloxy)ethyl]ethyl}amino)-β-D-glucopyranoside (409098-29-9)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / 10 percent Pd-C / ethyl acetate / 6 h / 20 °C

2: 3.80 g / ethyl acetate / 20 °C

3: 96 percent / NaOMe / methanol / 1 h / 20 °C

4: 64 percent / pyridine / 0 - 20 °C

5: 97 percent / pyridine / 12 h / 4 °C

6: 72 percent / NaN₃ / dimethylformamide / 24 h / 80 °C

7: 98 percent / NaOMe / methanol / 1 h / 20 °C

8: H₂ / 10 percent Pd-C / methanol / 10 h / 20 °C

9: 0.60 g / methanol / 18 h / 40 °C

10: 79 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; i-Pr₂NEt / dimethylformamide / 6 h / 45 °C

11: 100 percent / LiOH*H₂O / methanol; H₂O / 12 h / 0 °C

12: 56 percent / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; i-Pr₂NEt / dimethylformamide / 12 h / 45 °C

With pyridine; lithium hydroxide; sodium azide; hydrogen; sodium methylate; N-ethyl-N,N-diisopropylamine; HATU; palladium on activated charcoal; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; 9: Michael addition;

DOI:10.1002/1099-0690(20021)2002:1<79::AID-EJOC79>3.0.CO;2-1

upstream raw materials:

2-aminoethyl α-L-fucopyranoside

2-(tert-butyloxycarbonylamido)ethyl 6-deoxy-6-[{p-[(α-D-mannosyloxy)methyl]benzoyl}(2-propanoyl)amino]-β-D-glucopyranoside

di-tert-butyl dicarbonate

2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Downstream raw materials:

2-aminoethyl 6-deoxy-6-[{p-[(α-D-mannosyloxy)methyl]benzoyl}(2-{[2-(α-L-fucosyloxy)ethyl]carbamoyl}ethyl)amino]-β-D-glucopyranoside

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