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

Base Information

Chemical Name:4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-DL-phenylalanine
CAS No.:219826-30-9
Molecular Formula:C₁₇H₂₁NO₇
Molecular Weight:351.356
Hs Code.:

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

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

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

There total 7 articles about 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-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: 29.0%

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

: 219826-30-9
4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-DL-phenylalanine

: 219826-32-1
4-C-(3,7-anhydro-1-oxo-1,2-D-glycero-D-galactooctit-1-yl)-DL-phenylalanine

Guidance literature:: With hydrogenchloride; at 90 ℃; for 6h;
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

: 219826-30-9
4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-DL-phenylalanine

Guidance literature:: Multi-step reaction with 5 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

5: 29 percent / aq. HCl / 6 h / 90 °C

With piperidine; pyridine; hydrogenchloride; 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

: 219826-30-9
4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-DL-phenylalanine

Guidance literature:: Multi-step reaction with 6 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

6: 29 percent / aq. HCl / 6 h / 90 °C

With piperidine; pyridine; hydrogenchloride; 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