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

Base Information

• Chemical Name: 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-L-phenylalanine
• CAS No.: 219826-31-0
• Molecular Formula: C₁₇H₂₁NO₇
• Molecular Weight: 351.356
• Mol file: 219826-31-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-L-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: 62.0%

N-acetyl 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-mannooctityl)-DL-phenylalanine (219826-24-1) → 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-L-phenylalanine (219826-31-0)

Guidance literature:

for 48h; Ambient temperature; PBS buffer (pH=7.5); enzymatic hydrolysis by acylase I from Aspergillus melleus;

DOI:10.1021/jo980517h

Reference yield:

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 (219864-01-4) → 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-L-phenylalanine (219826-31-0)

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: 62 percent / 48 h / Ambient temperature; PBS buffer (pH=7.5); enzymatic hydrolysis by acylase I from Aspergillus melleus

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 → 4-C-(3,7-anhydro-1,1,2,2-tetradehydro-1,2-D-glycero-D-galactooctityl)-L-phenylalanine (219826-31-0)

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: 62 percent / 48 h / Ambient temperature; PBS buffer (pH=7.5); enzymatic hydrolysis by acylase I from Aspergillus melleus

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

upstream raw materials:

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

N-acetyl-4-iodo-(DL)-phenylalanine methyl ester

3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol