Tetra-O-acetyl-a-Mannosyl-Fmocserine

Base Information

• Chemical Name: Tetra-O-acetyl-a-Mannosyl-Fmocserine
• CAS No.: 118358-80-8
• Molecular Formula: C32H35 N O14
• Molecular Weight: 657.628
• Mol file: 118358-80-8.mol

Synonyms:Tetra-O-acetyl-a-Mannosyl-Fmocserine

Chemical Property of Tetra-O-acetyl-a-Mannosyl-Fmocserine

Chemical Property:

• PSA: 221.29000
• LogP: 1.27520

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl-Fmoc serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl-Fmoc serine (CAS# 118358-80-8) is a an fmoc-protected, and glycosylated form of L-serine (S270995) used in the synthetic preparation of peptides and peptide fragments, such as the synthesis of homogeneously glycosylated insulin for use as an oral medication for diabetics.

Technology Process of Tetra-O-acetyl-a-Mannosyl-Fmocserine

There total 11 articles about Tetra-O-acetyl-a-Mannosyl-Fmocserine 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%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-2-Amino-3-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid (935457-93-5) → N-(9-fluorenylmethyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine (118358-80-8)

Guidance literature:

In 1,4-dioxane; at 20 ℃; for 1h; pH=8.5;

DOI:10.1021/jo005712m

Reference yield: 95.0%

N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine allyl ester (168566-64-1) → N-(9-fluorenylmethyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine (118358-80-8)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; for 0.5h; Inert atmosphere;

DOI:10.1039/b902455g

Reference yield: 85.0%

2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid allyl ester → O1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-Nα-(fluoren-9-ylmethoxycarbonyl)serine (96383-44-7,118358-38-6,118358-80-8,128924-12-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1039/C39900000965

upstream raw materials:

2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionic acid allyl ester

N-Fmoc-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine benzyl ester

D-Mannose pentaacetate

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Downstream raw materials:

-D-glutamic acid 1-methylamide 5-benzyl ester

-L-glutamic acid 1-methylamide 5-benzyl ester

-D-glutamic acid 1-methylamide 5-benzyl ester

-L-glutamic acid 1-methylamide 5-benzyl ester

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