(2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid

Base Information

• Chemical Name: (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid
• CAS No.: 1357485-67-6
• Molecular Formula: C₂₆H₂₃NO₇
• Molecular Weight: 461.471
• Mol file: 1357485-67-6.mol

Synonyms:(2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid

Chemical Property of (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid

There total 1 articles about (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid 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: 96.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S,3S)-2-amino-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid (19516-01-9) → (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid (1357485-67-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; for 2h;

DOI:10.1007/s00726-010-0806-x

Reference yield: 65.0%

3,4-dihydro-2H-pyran (110-87-2) + (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid (1357485-67-6) → (2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-4-oxo-3-(tetrahydro-2H-pyran-2-yloxy)butanoic acid (1357485-68-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1007/s00726-010-0806-x

Reference yield:

(2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid (1357485-67-6) → (2S,3S)-1-allyl 4-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tetrahydro-2H-pyran-2-yloxy)succinate (1357485-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / dichloromethane / 72 h / 20 °C

2: Aliquat 336; sodium hydrogencarbonate / dichloromethane; water / 72 h / 20 °C

With pyridinium p-toluenesulfonate; Aliquat 336; sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1007/s00726-010-0806-x

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,3S)-2-amino-4-(benzyloxy)-3-hydroxy-4-oxobutanoic acid

Downstream raw materials:

(2S,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(benzyloxy)-4-oxo-3-(tetrahydro-2H-pyran-2-yloxy)butanoic acid

(2S,3S)-1-allyl 4-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tetrahydro-2H-pyran-2-yloxy)succinate