L-Serine, N-[(phenylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-, methyl ester

Base Information

• Chemical Name: L-Serine, N-[(phenylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-, methyl ester
• CAS No.: 25644-83-1
• Molecular Formula: C₂₆H₃₄N₂O₁₃
• Molecular Weight: 582.562
• NSC Number: 173939
• DSSTox Substance ID: DTXSID60306055
• Mol file: 25644-83-1.mol

Synonyms:25644-83-1;NSC173939;Alanine, N-benzyl methyl ester, 3',4',6'-triacetate, L-;DTXSID60306055;ZINC05179522;NSC-173939;L-Serine,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-.beta.-D-glucopyranosyl]-, methyl ester;Methyl 3-({3-acetamido-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl}oxy)-2-{[(benzyloxy)carbonyl]amino}propanoate (non-preferred name)

Chemical Property of L-Serine, N-[(phenylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-, methyl ester

Chemical Property:

• Vapor Pressure: 7.96E-22mmHg at 25°C
• Boiling Point: 741°Cat760mmHg
• Flash Point: 401.9°C
• PSA: 191.09000
• Density: 1.32g/cm³
• LogP: 0.90890
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 17
• Exact Mass: 582.20608914
• Heavy Atom Count: 41
• Complexity: 936

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCC(C(=O)OC)NC(=O)OCC2=CC=CC=C2)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of L-Serine, N-[(phenylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-, methyl ester

There total 2 articles about L-Serine, N-[(phenylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-, methyl ester 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: 30.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N-(benzyloxycarbonyl)serin-methylester (25644-83-1)

Guidance literature:

With mercury(II) cyanide; In benzene;

DOI:10.1002/jlac.198319830303

Reference yield:

→ O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N-(benzyloxycarbonyl)serin-methylester (25644-83-1)

Guidance literature:

2-Methyl-4,5-(2-acetamino-3,4,6-tri-O-acetyl-2-desoxy-α-D-glucopyrano)-Δ²-oxazolin, Z-Ser-OMe;

Reference yield:

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N-(benzyloxycarbonyl)serin-methylester (25644-83-1) → N2-(Benzyloxycarbonyl)asparaginyl-leucyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester (86041-04-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / H₂ / 10percent Pd/C / methanol / 3 h / Ambient temperature

2: 74 percent / (ethyl)-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / CHCl₃ / 1) 1 h, -15 deg C, 2) room temperature, 15 h

3: 76 percent / morpholine / CH₂Cl₂ / 0.33 h / Ambient temperature

4: 41 percent / (ethyl)-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / dimethylformamide / 48 h / Ambient temperature

With morpholine; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; palladium on activated charcoal; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/jlac.198319830303

upstream raw materials:

N-benzyloxycarbonyl-L-serine methyl ester

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

N-<2-(Triphenylphosphonio)ethoxycarbonyl>phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

N-<2-(Triphenylphosphonio)ethoxycarbonyl>leucyl-leucyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

N-<2-(Triphenylphosphonio)ethoxycarbonyl>isoleucyl-phenylalanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester-chlorid

Leucyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)serin-methylester