2-[4,5-Dihydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Base Information

• Chemical Name: 2-[4,5-Dihydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS No.: 98302-29-5
• Molecular Formula: C₁₅H₂₈O₁₁
• Molecular Weight: 384.381
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID70394660
• Mol file: 98302-29-5.mol

Synonyms:98302-29-5;2-[4,5-dihydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;SCHEMBL17263250;SCHEMBL19682315;SCHEMBL20438916;DTXSID70394660;propyl 4-O-hexopyranosylhexopyranoside;FT-0774395

Chemical Property of 2-[4,5-Dihydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 9.11E-20mmHg at 25°C
• Refractive Index: 1.591
• Boiling Point: 652.1 °C at 760 mmHg
• Flash Point: 348.2 °C
• PSA: 178.53000
• Density: 1.53 g/cm³
• LogP: -3.96290
• Storage Temp.: −20°C
• 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:

99%min. ^*data from raw suppliers

N-Propyl b-lactoside ^*data from reagent suppliers

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

Technology Process of 2-[4,5-Dihydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

There total 18 articles about 2-[4,5-Dihydroxy-2-(hydroxymethyl)-6-propoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 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:

propan-1-ol (71-23-8) + β‐cyclodextrin (7585-39-9) → propyl α-D-glucopyranoside (25320-91-6,34384-77-5,39824-08-3,62178-32-9,63223-88-1,73351-01-6,95586-01-9,118245-33-3,118245-34-4) + propyl-α-D-maltotrioside + propyl-α-D-maltopyranoside (98302-29-5)

Guidance literature:

With recombinant cyclodextrin glycosyltransferase from the Bacillus circulans A₁₁; In aq. phosphate buffer; at 50 ℃; for 96h; pH=6; Concentration; Time; Temperature; pH-value; Enzymatic reaction;

DOI:10.1007/s12257-016-0013-z

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

upstream raw materials:

diphosphoric acid 1''-β-D-[1'']glucopyranosyl ester 2-(uridin-5'-yl)ester

propyl β-D-glucopyranoside

(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

Refernces

• 1、 Charoensapyanan, Rittichai,Ito, Kazuo,Rudeekulthamrong, Prakarn,Kaulpiboon, Jarunee. "Enzymatic synthesis of propyl-α-glycosides and their application as emulsifying and antibacterial agents". . p. 389 - 401. Retrieved 2016/07/30.