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

Base Information

• Chemical Name: 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
• CAS No.: 142889-23-4
• Molecular Formula: C₅₅H₆₈N₂O₁₆
• Molecular Weight: 1013.15

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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:

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → 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 (142889-23-4)

Guidance literature:

Multi-step reaction with 5 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

4: H₂S, Et₃N / H₂O; pyridine / 1 h

5: pyridine / 4 h

With pyridine; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen sulfide; triethylamine; trifluoroacetic acid; In pyridine; diethyl ether; water; 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-(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 (142889-23-4)

Guidance literature:

Multi-step reaction with 6 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

5: H₂S, Et₃N / H₂O; pyridine / 1 h

6: pyridine / 4 h

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

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

Reference yield:

1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose (136172-58-2) → 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 (142889-23-4)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: H₂S, Et₃N / H₂O; pyridine / 1 h

4: pyridine / 4 h

With pyridine; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen sulfide; triethylamine; In pyridine; diethyl ether; water; 1,2-dichloro-ethane;

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

upstream raw materials:

acetic anhydride

benzyl bromide

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

1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose

Downstream raw materials:

(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

(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

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