(2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid
• CAS No.: 18409-15-9
• Molecular Formula: C₃₄H₅₆N₂O₂₇
• Molecular Weight: 924.816
• Metabolomics Workbench ID: 38996
• Nikkaji Number: J2.987.837D
• Mol file: 18409-15-9.mol

Synonyms:alphaNeu5Ac(2,8)alphaNeu5Ac(2,3)betaDGal(1,4)DGlc;di-(N-acetylneuramin)lactose;disialyl lactose;disialyllactose

Chemical Property of (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Boiling Point: 1415.3°Cat760mmHg
• Flash Point: 809.7°C
• PSA: 487.61000
• Density: 1.78g/cm³
• LogP: -9.36900
• Storage Temp.: −20°C
• XLogP3: -9.7
• Hydrogen Bond Donor Count: 18
• Hydrogen Bond Acceptor Count: 27
• Rotatable Bond Count: 18
• Exact Mass: 924.30704451
• Heavy Atom Count: 63
• Complexity: 1570

Purity/Quality:

96% ^*data from raw suppliers

Disialyllactose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(CC(OC1C(C(CO)OC2(CC(C(C(O2)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)(C(=O)O)OC3C(C(OC(C3O)OC4C(OC(C(C4O)O)O)CO)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O[C@@]2(C[C@@H]([C@H]([C@@H](O2)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)(C(=O)O)O[C@H]3[C@H]([C@H](O[C@H]([C@@H]3O)O[C@@H]4[C@H](OC([C@@H]([C@H]4O)O)O)CO)CO)O)O

Technology Process of (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid

There total 2 articles about (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic 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:

sialic acid (489-46-3,6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) + 3'-sialyllactose (18409-13-7,64839-32-3,64839-33-4,102778-91-6,102778-92-7) → α-Neup5Ac-(2->8)-α-Neup5Ac-(2->3)-β-D-Galp-(1->4)-D-Glc (18409-15-9)

Guidance literature:

With Neisseria meningitidis CMP-sialic acid synthetase; Campylobacter jejuni α2?3/8-sialyltransferase; sodium pyruvate; cytidine triphosphate; magnesium chloride; In aq. buffer; at 37 ℃; pH=8.5; Enzymatic reaction;

DOI:10.1021/acs.joc.6b01905

Reference yield:

sialic acid (489-46-3,6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → α-Neup5Ac-(2->8)-α-Neup5Ac-(2->3)-β-D-Galp-(1->4)-D-Glc (18409-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: cytidine triphosphate; magnesium chloride; sodium pyruvate; Pasteurella multocida α2?3-sialyltransferase 1 M144D mutant; Neisseria meningitidis CMP-sialic acid synthetase / aq. buffer / 37 °C / pH 8.5 / Enzymatic reaction

2: cytidine triphosphate; magnesium chloride; sodium pyruvate; Neisseria meningitidis CMP-sialic acid synthetase; Campylobacter jejuni α2?3/8-sialyltransferase / aq. buffer / 37 °C / pH 8.5 / Enzymatic reaction

With Neisseria meningitidis CMP-sialic acid synthetase; Campylobacter jejuni α2?3/8-sialyltransferase; Pasteurella multocida α2?3-sialyltransferase 1 M144D mutant; sodium pyruvate; cytidine triphosphate; magnesium chloride; In aq. buffer;

DOI:10.1021/acs.joc.6b01905

upstream raw materials:

sialic acid

3'-sialyllactose