alpha-C-Mannosyltryptophan

Base Information

• Chemical Name: alpha-C-Mannosyltryptophan
• CAS No.: 180509-18-6
• Molecular Formula: C₁₇H₂₂N₂O₇
• Molecular Weight: 366.371
• Nikkaji Number: J1.147.090D
• Wikidata: Q104967834
• Metabolomics Workbench ID: 78578
• Mol file: 180509-18-6.mol

Synonyms:2(MP)-L-T;2-(alpha-mannopyranosyl)-L-tryptophan;2-(mannopyranosyl)-tryptophan

Chemical Property of alpha-C-Mannosyltryptophan

Chemical Property:

• Melting Point: >145°C (dec.)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 366.14270105
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

2-(α-D-Mannopyranosyl)-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)C3C(C(C(C(O3)CO)O)O)O)CC(C(=O)O)N
• Isomeric SMILES: C1=CC=C2C(=C1)C(=C(N2)[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C[C@@H](C(=O)O)N
• Uses: 2-(α-D-Mannopyranosyl)-L-tryptophan is a tryptophan glycoconjugate being tested as an diagnostic tool for the accurate measure of renal function. 2-(α-D-Mannopyranosyl)-L-tryptophan is a tryptophan glycoconjugate being tested as a diagnostic tool for the accurate measure of renal function.

Technology Process of alpha-C-Mannosyltryptophan

There total 19 articles about alpha-C-Mannosyltryptophan 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: 71.0%

2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan → α-C-Mannosyltryptophan (180509-18-6)

Guidance literature:

With hydrogenchloride; hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 3h;

DOI:10.1039/b414905j

Reference yield: 67.0%

α-azido-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid (252187-25-0) → α-C-Mannosyltryptophan (180509-18-6)

Guidance literature:

With hydrogen; 20percent Pd(OH)2/C; In 1,4-dioxane; water; at 40 ℃; for 48h;

DOI:10.1002/chem.200390163

Reference yield:

2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole (358620-68-5) → α-C-Mannosyltryptophan (180509-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Sc(OTf)3 / CH₂Cl₂ / 3 h / 0 °C

2: 70 percent / aq. LiOH / propan-2-ol / 2 h / 20 °C

3: 71 percent / H₂; aq. HCl / Pd(OH)2/C / methanol / 3 h / 20 °C

With hydrogenchloride; lithium hydroxide; hydrogen; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; In methanol; dichloromethane; isopropyl alcohol;

DOI:10.1039/b414905j

upstream raw materials:

α-azido-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside

8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol

2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

Refernces

• 1、 Nishikawa, Toshio,Koide, Yuya,Kajii, Shigeo,Wada, Kyoko,Ishikawa, Miyuki,Isobe, Minoru. "Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues". . p. 687 - 700. Retrieved 2007/10/03.