3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannopyrannose

Base Information

• Chemical Name: 3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannopyrannose
• CAS No.: 121123-33-9
• Molecular Formula: C₁₈H₃₂O₁₆
• Molecular Weight: 504.442
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID20392999
• Wikidata: Q82191590
• Mol file: 121123-33-9.mol

Synonyms:121123-33-9;3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannopyrannose;2-(hydroxymethyl)-6-[[3,5,6-trihydroxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol;3,6-Di-o-(a-D-mannopyranosyl)-D-mannopyranose;3,6-DI-O-(ALPHA-D-MANNO-PYRANOSYL)-D-MANNO-PYRANOSE;3.alpha.,6.alpha.-Mannotriose;SCHEMBL18755587;SCHEMBL20869883;SCHEMBL22296764;DTXSID20392999;KJZMZIMBDAXZCX-UHFFFAOYSA-N;AKOS030254252;AS-78668;FT-0614768;3,6-DI-O-(A-D-MANNOPYRANOSYL)-D-MANNOPYRANNOSE;hexopyranosyl-(1->3)-[hexopyranosyl-(1->6)]hexopyranose;.alpha.-D-Mannopyranose, O-.alpha.-D-mannopyranosyl-(1->3)-O-[.alpha.-D-mannopyranosyl-(1->6)]-

Chemical Property of 3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannopyrannose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 140-145掳C
• Refractive Index: 1.673
• Boiling Point: 879.4°C at 760 mmHg
• PKA: 11.97±0.70(Predicted)
• Flash Point: 485.6°C
• PSA: 268.68000
• Density: 1.8g/cm³
• LogP: -7.57300
• Storage Temp.: −20°C
• Solubility.: Water (Slightly)
• XLogP3: -6.3
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 7
• Exact Mass: 504.16903493
• Heavy Atom Count: 34
• Complexity: 641

Purity/Quality:

99% ^*data from raw suppliers

1,3-a-1,6-a-D-Mannotriose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)O)O)OC3C(C(C(C(O3)CO)O)O)O)O)O)O)O)O
• Uses: Mannotriose core structure of n-linked oligosaccharides. Of potential interest in the development of conjugated vaccine.

Technology Process of 3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannopyrannose

There total 13 articles about 3,6-Di-O-(alpha-D-mannopyranosyl)-D-mannopyrannose 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: 44.0%

benzyl 2,4-di-O-benzyl-3,6-di-O-β-D-glucopyranosyl-α-D-glucopyranoside (82186-24-1,103078-30-4) → O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-α,β-D-glucopyranose (3256-10-8,75597-63-6,78039-04-0,78039-05-1,95463-61-9,121123-33-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; at 20 ℃; for 72h;

DOI:10.1016/S0008-6215(82)80007-4

Reference yield:

benzyl 4,6-O-benzylidene-α-D-glucopyranoside (186697-04-1) → O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-α,β-D-glucopyranose (3256-10-8,75597-63-6,78039-04-0,78039-05-1,95463-61-9,121123-33-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Bu₂SnO / 1.) benzene, MeOH, reflux, 2.5 h; 2.) DMF, 100-120 deg C, 3.5 h

2: 53 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

3: 47 percent / powdered molecular sieve 4 A, HgBr₂ / 1,2-dichloro-ethane / 24 h / 45 °C

4: 95 percent / MeOH / 1 M NaOMe / 15 h / 20 °C

5: 44 percent / hydrogen / 10 percent Pd-C / ethanol; H₂O / 72 h / 20 °C

With methanol; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; hydrogen; di(n-butyl)tin oxide; mercury dibromide; palladium on activated charcoal; sodium methylate; In diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(82)80007-4

Reference yield:

benzyl D-glucopyranoside (34246-23-6) → O-β-D-glucopyranosyl-(1-3)-O-<β-D-glucopyranosyl-(1-6)>-α,β-D-glucopyranose (3256-10-8,75597-63-6,78039-04-0,78039-05-1,95463-61-9,121123-33-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) TsOH*H₂O; 2.) Et₃N / dimethylformamide / 2 h / 40 - 45 °C

2: 1.) Bu₂SnO / 1.) benzene, MeOH, reflux, 2.5 h; 2.) DMF, 100-120 deg C, 3.5 h

3: 53 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

4: 47 percent / powdered molecular sieve 4 A, HgBr₂ / 1,2-dichloro-ethane / 24 h / 45 °C

5: 95 percent / MeOH / 1 M NaOMe / 15 h / 20 °C

6: 44 percent / hydrogen / 10 percent Pd-C / ethanol; H₂O / 72 h / 20 °C

With methanol; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; hydrogen; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; mercury dibromide; palladium on activated charcoal; sodium methylate; In diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(82)80007-4

upstream raw materials:

6²-β-D-glucopyranosyl-laminaratriose

benzyl 2,4-di-O-benzyl-3,6-di-O-β-D-glucopyranosyl-α-D-glucopyranoside

benzyl 4,6-O-benzylidene-α-D-glucopyranoside

benzyl D-glucopyranoside

Refernces

• 1、 Koto, Shinkiti,Morishima, Naohiko,Kusuhara, Chiharu,Sekido, Shigeko,Yoshida, Toyosaku,Zen, Shonosuke. "Stereoselective α-Glucosylation with Tetra-O-benzyl-α-D-glucose and a Mixture of Trimethylsilyl Bromide, Cobalt(II) Bromide, Tetrabutylammonium Bromide, and a Molecular Sieve. A Synthesis of 3,6-Di-O-(α-D-glucopyranosyl)-D-glucose". . p. 2995 - 2999. Retrieved 2007/10/02.
• 2、 Yoshimitsu, Ueno,Masatoshi, Abe. "A new, crystalline glucotetraose (62-β-D-glucopyranosyl-laminaratriose)". . p. 151 - 155. Retrieved 2007/10/02.