ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

Base Information

• Chemical Name: ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate
• CAS No.: 142889-22-3
• Molecular Formula: C₅₃H₆₄N₄O₁₅
• Molecular Weight: 997.109

Synonyms:ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

Chemical Property of ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

There total 10 articles about ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate 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: 70.0%

ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside (157967-50-5) + ethyl (N-benzyloxycarbonyl 3-aminopropyl-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate (142889-21-2) → ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate (142889-22-3)

Guidance literature:

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane; for 0.25h;

DOI:10.1016/S0040-4020(01)81239-4

Reference yield:

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate (142889-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / CF₃COOH / 4 h / 50 °C

2: 71 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 1 h / 35 °C

3: 70 percent / N-iodosuccinimide, molecular sieves, triflic acid / 1,2-dichloro-ethane; diethyl ether / 0.25 h

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; trifluoroacetic acid; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)81239-4

Reference yield:

benzyl bromide (100-39-0) → ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate (142889-22-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaH / dimethylformamide / 1 h

2: 95 percent / CF₃COOH / 4 h / 50 °C

3: 71 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 1 h / 35 °C

4: 70 percent / N-iodosuccinimide, molecular sieves, triflic acid / 1,2-dichloro-ethane; diethyl ether / 0.25 h

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; sodium hydride; trifluoroacetic acid; In diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)81239-4

upstream raw materials:

ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside

ethyl (N-benzyloxycarbonyl 3-aminopropyl-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

benzyl bromide

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

Downstream raw materials:

(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid

(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

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