N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide

Base Information

• Chemical Name: N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide
• CAS No.: 186585-76-2
• Molecular Formula: C₄₅H₆₆N₂O₅
• Molecular Weight: 715.029

Synonyms:N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide

Chemical Property of N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide

There total 12 articles about N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide 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: 99.0%

Tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester (186585-89-7) → N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide (186585-76-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4039(96)02121-1

Reference yield:

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide (186585-76-2)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine

2: BF₃*OEt₂, TMSOTf / acetonitrile / 0 °C

3: NaOMe / methanol

4: NaH, TBAI / tetrahydrofuran

5: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) -78 deg C to 23 deg C

6: Et₃N, MgSO₄ / CH₂Cl₂

7: NaBH₄ / methanol / 0 °C

8: CH₂Cl₂

9: 95 percent / LiOH / methanol; H₂O / 4 °C

10: 70 percent / EDC, NMM / CHCl₃ / 0 - 23 °C

11: 99 percent / TFA / CH₂Cl₂

With 4-methyl-morpholine; lithium hydroxide; sodium tetrahydroborate; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium sulfate; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetonitrile;

DOI:10.1016/S0040-4039(96)02121-1

Reference yield:

benzyl bromide (100-39-0) → N-Tetradecyl-2-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylamino]-acetamide (186585-76-2)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH, TBAI / tetrahydrofuran

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) -78 deg C to 23 deg C

3: Et₃N, MgSO₄ / CH₂Cl₂

4: NaBH₄ / methanol / 0 °C

5: CH₂Cl₂

6: 95 percent / LiOH / methanol; H₂O / 4 °C

7: 70 percent / EDC, NMM / CHCl₃ / 0 - 23 °C

8: 99 percent / TFA / CH₂Cl₂

With 4-methyl-morpholine; lithium hydroxide; sodium tetrahydroborate; dimethylsulfide; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium sulfate; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;

DOI:10.1016/S0040-4039(96)02121-1

upstream raw materials:

Tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester

6-deoxy-L-galactose

benzyl bromide

1,2,3,4-tetra-O-acetyl-L-fucopyranose

Downstream raw materials:

4-((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propylcarbamoyl)-butyric acid benzyl ester

((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propyl)-carbamic acid tert-butyl ester

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