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

Base Information

Chemical Name:Tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester
CAS No.:186585-89-7
Molecular Formula:C₅₀H₇₄N₂O₇
Molecular Weight:815.147
Hs Code.:

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

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

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

There total 11 articles about Tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid tert-butyl ester 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%

: 2016-42-4
tetradecylamine

: 186585-87-5
{tert-Butoxycarbonyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-amino}-acetic acid

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

Guidance literature:: With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In chloroform; at 0 - 23 ℃;
DOI:10.1016/S0040-4039(96)02121-1

Reference yield:

: 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
6-deoxy-L-galactose

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

Guidance literature:: Multi-step reaction with 10 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

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; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetonitrile;
DOI:10.1016/S0040-4039(96)02121-1

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 7 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

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; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;
DOI:10.1016/S0040-4039(96)02121-1