N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

Base Information

Chemical Name:N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine
CAS No.:219826-24-1
Molecular Formula:C₁₉H₂₃NO₈
Molecular Weight:393.394
Hs Code.:

Synonyms:N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

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Chemical Property of N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

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Technology Process of N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

There total 6 articles about N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine 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: 97.0%

: 219826-16-1
N-acetyl 4-C-(3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine methyl ester

: 219826-24-1
N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

Guidance literature:: With methanol; sodium; for 2h; Ambient temperature;
DOI:10.1021/jo980517h

Reference yield:

: 219864-01-4
3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol

: 219826-24-1
N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / aq. NaOH / methanol; CH₂Cl₂ / 1 h / Ambient temperature

2: 81 percent / TMSOTf / 72 h / Ambient temperature

3: 1.) (Ph₃P)4Pd, CuI, piperidine, 2.) pyridine / 1) 80 deg C, 1 h; 2) overnight, rt

4: 97 percent / Na, CH₃OH / 2 h / Ambient temperature

With piperidine; pyridine; methanol; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; sodium; In methanol; dichloromethane;
DOI:10.1021/jo980517h

Reference yield:

: 4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-galactooct-3-ulopyranose

: 219826-24-1
N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Et₃SiH, 2.) BF₃OEt₂ / 1) CH₃CN, CH₂Cl₂, -10 deg C; 2) CH₃CN, CH₂Cl₂, -10 deg C, 1 h

2: 99 percent / aq. NaOH / methanol; CH₂Cl₂ / 1 h / Ambient temperature

3: 81 percent / TMSOTf / 72 h / Ambient temperature

4: 1.) (Ph₃P)4Pd, CuI, piperidine, 2.) pyridine / 1) 80 deg C, 1 h; 2) overnight, rt

5: 97 percent / Na, CH₃OH / 2 h / Ambient temperature

With piperidine; pyridine; methanol; triethylsilane; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium; In methanol; dichloromethane;
DOI:10.1021/jo980517h