1-Propyl-4-O-beta galactopyranosyl-alpha galactopyranoside

Base Information

• Chemical Name: 1-Propyl-4-O-beta galactopyranosyl-alpha galactopyranoside
• CAS No.: 93496-18-5
• Molecular Formula: C₁₅H₂₈O₁₁
• Molecular Weight: 384.381
• DSSTox Substance ID: DTXSID30239442
• Wikidata: Q83121801
• Mol file: 93496-18-5.mol

Synonyms:1-propyl-4-O-beta galactopyranosyl-alpha galactopyranoside;PBGAG

Chemical Property of 1-Propyl-4-O-beta galactopyranosyl-alpha galactopyranoside

Chemical Property:

• Vapor Pressure: 9.11E-20mmHg at 25°C
• Boiling Point: 652.1°C at 760 mmHg
• Flash Point: 348.2°C
• PSA: 178.53000
• Density: 1.53g/cm³
• LogP: -3.96290
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 384.16316171
• Heavy Atom Count: 26
• Complexity: 424

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCOC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O
• Isomeric SMILES: CCCO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O

Technology Process of 1-Propyl-4-O-beta galactopyranosyl-alpha galactopyranoside

There total 16 articles about 1-Propyl-4-O-beta galactopyranosyl-alpha galactopyranoside 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: 85.0%

(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Allyloxy-4-benzyloxy-2-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3,5-diol (93496-17-4) → propyl 4-O-β-D-galactopyranosyl-α-D-galactopyranoside (93496-18-5,98302-29-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; for 72h;

DOI:10.1016/0008-6215(84)85244-1

Reference yield:

allyl 6-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside (6207-47-2) → propyl 4-O-β-D-galactopyranosyl-α-D-galactopyranoside (93496-18-5,98302-29-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / pyridine

2: 0.5 M HCl / methanol

3: 1.) methanol, reflux, 1.5 h, 2.) DMF, heating, 2 h

4: 96 percent / C₅H₅N

5: tris(phenylphosphine)rhodium(I) chloride / aq. ethanol / 2 h / Heating

6: 1.) mercuric oxide, mercuric chloride, water, 2.) HCl / 1.) aq. ethanol, refl., 2 h, 2.) diethyl ether, RT, 24 h

7: acetonitrile / 0.5 h / Ambient temperature

8: acetonitrile / 48 h / Ambient temperature

9: 67 percent / 2 percent KCN, H₂O / ethanol

10: 85 percent / H₂ / 10 percent palladium-on-carbon / ethanol; H₂O / 72 h

With pyridine; hydrogenchloride; potassium cyanide; tris(phenylphosphine)rhodium(I) chloride; water; hydrogen; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In methanol; ethanol; water; acetonitrile;

DOI:10.1016/0008-6215(84)85244-1

Reference yield:

allyl 2-O-benzoyl-6-O-benzyl-α-D-galactopyranoside (78878-42-9) → propyl 4-O-β-D-galactopyranosyl-α-D-galactopyranoside (93496-18-5,98302-29-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) methanol, reflux, 1.5 h, 2.) DMF, heating, 2 h

2: 96 percent / C₅H₅N

3: tris(phenylphosphine)rhodium(I) chloride / aq. ethanol / 2 h / Heating

4: 1.) mercuric oxide, mercuric chloride, water, 2.) HCl / 1.) aq. ethanol, refl., 2 h, 2.) diethyl ether, RT, 24 h

5: acetonitrile / 0.5 h / Ambient temperature

6: acetonitrile / 48 h / Ambient temperature

7: 67 percent / 2 percent KCN, H₂O / ethanol

8: 85 percent / H₂ / 10 percent palladium-on-carbon / ethanol; H₂O / 72 h

With pyridine; hydrogenchloride; potassium cyanide; tris(phenylphosphine)rhodium(I) chloride; water; hydrogen; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In ethanol; water; acetonitrile;

DOI:10.1016/0008-6215(84)85244-1

upstream raw materials:

(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Allyloxy-4-benzyloxy-2-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3,5-diol

allyl 6-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside

4-O-acetyl-2-O-benzoyl-3,6-di-O-benzyl-α-D-galactopyranosyl chloride

allyl 2-O-benzoyl-6-O-benzyl-α-D-galactopyranoside

Refernces