N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside

Base Information

• Chemical Name: N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside
• CAS No.: 128775-49-5
• Molecular Formula: C₃₉H₃₉NO₁₁
• Molecular Weight: 697.739

Synonyms:N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside

Chemical Property of N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside

There total 8 articles about N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-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: 85.0%

1-O-(2-methylbenzoyloxy)benzotriazole (128775-55-3) + N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-β-D-glucopyranoside (128775-48-4) → N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside (128775-49-5)

Guidance literature:

With triethylamine; In 1,2-dichloro-ethane; for 17h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89206-1

Reference yield:

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) → N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside (128775-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / mercuric bromide, mercuric cyanide / acetonitrile / 4 h / Ambient temperature

2: 98 percent / NaOMe / methanol / 17 h / Ambient temperature

3: 79 percent / p-TsOH / acetone / 4 h / Ambient temperature

4: pyridine / 2 h / Ambient temperature

5: H₂O / acetic acid / 1 h / 50 °C

6: 85 percent / Et₃N / 1,2-dichloro-ethane / 17 h / Ambient temperature

With pyridine; water; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; triethylamine; mercury dibromide; In methanol; acetic acid; 1,2-dichloro-ethane; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)89206-1

Reference yield:

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-6-O-(2-methylbenzoyl)-β-D-glucopyranoside (128775-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / mercuric bromide, mercuric cyanide / acetonitrile / 4 h / Ambient temperature

2: 98 percent / NaOMe / methanol / 17 h / Ambient temperature

3: 79 percent / p-TsOH / acetone / 4 h / Ambient temperature

4: pyridine / 2 h / Ambient temperature

5: H₂O / acetic acid / 1 h / 50 °C

6: 85 percent / Et₃N / 1,2-dichloro-ethane / 17 h / Ambient temperature

With pyridine; water; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; triethylamine; mercury dibromide; In methanol; acetic acid; 1,2-dichloro-ethane; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)89206-1

upstream raw materials:

1-O-(2-methylbenzoyloxy)benzotriazole

N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-β-D-glucopyranoside

2,3,4,6-tetra-O-benzoylglucosyl bromide

3-[(N-benzyloxycarbonyl)amino]propanol

Downstream raw materials:

N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-4-O-<2,3-di-O-(2-methylbenzoyl)-4-O-dichloroacetyl-α-L-rhamnopyranosyl>-6-O-(2-methylbenzoyl)-β-D-glucopyranoside

N-benzyloxycarbonyl-3-aminopropyl 2,3-di-O-benzoyl-4-O-<2,3-di-O-(2-methylbenzoyl)-α-L-rhamnopyranosyl>-6-O-(2-methylbenzoyl)-β-D-glucopyranoside

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