.beta.-D-Allopyranoside, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-4-yl 2-(acetylamino)-4-O-2-(acetylamino)-2-deoxy-.beta.-D-allopyranosyl-2-deoxy-, 3aS-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-

Base Information

• Chemical Name: .beta.-D-Allopyranoside, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-4-yl 2-(acetylamino)-4-O-2-(acetylamino)-2-deoxy-.beta.-D-allopyranosyl-2-deoxy-, 3aS-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-
• CAS No.: 158528-74-6
• Molecular Formula: C₂₅H₄₂N₄O₁₄
• Molecular Weight: 622.627
• Mol file: 158528-74-6.mol

Synonyms:4H-Cyclopentoxazole,b-D-allopyranoside deriv.

Chemical Property of .beta.-D-Allopyranoside, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-4-yl 2-(acetylamino)-4-O-2-(acetylamino)-2-deoxy-.beta.-D-allopyranosyl-2-deoxy-, 3aS-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-

Chemical Property:

• PKA: 12.75±0.70(Predicted)
• Density: 1.78±0.1 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of .beta.-D-Allopyranoside, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-4-yl 2-(acetylamino)-4-O-2-(acetylamino)-2-deoxy-.beta.-D-allopyranosyl-2-deoxy-, 3aS-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-

There total 22 articles about .beta.-D-Allopyranoside, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-6-(hydroxymethyl)-4H-cyclopentoxazol-4-yl 2-(acetylamino)-4-O-2-(acetylamino)-2-deoxy-.beta.-D-allopyranosyl-2-deoxy-, 3aS-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)- 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: 92.0%

(1S,5S)-8-exo-benzyloxymethyl-3-dimethylamino-7-endo-hydroxy-2-oxa-4-azabicyclo<3.3.0>oct-3-en-6-endo-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside → (1S,5S)-3-dimethylamino-8-exo-hydroxymethyl-7-endo-hydroxy-2-oxa-4-azabicyclo<3.3.0>oct-3-en-6-endo-yl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-allopyranosyl)-2-deoxy-β-D-allopyranoside (158528-74-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; for 96h; under 2844.3 Torr;

Reference yield:

allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside (65947-37-7) → (1S,5S)-3-dimethylamino-8-exo-hydroxymethyl-7-endo-hydroxy-2-oxa-4-azabicyclo<3.3.0>oct-3-en-6-endo-yl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-allopyranosyl)-2-deoxy-β-D-allopyranoside (158528-74-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / pyridine / 16 h / 4 °C

2: 91 percent / sodium acetate / 2-methoxy-ethanol; H₂O / 9 h / 125 °C

3: 94 percent / barium oxide, barium hydroxide / dimethylformamide / 16 h / 20 °C

4: 1.) KOH / 1.) CH₃OH, H₂O, 125 deg C, 5 d, 2.) CHCl₃, 20 deg C, 20 min

5: 89 percent / 2)2>PF₆ / tetrahydrofuran / 1.5 h

6: 91 percent / HgCl₂ / acetone; H₂O / 3 h / 20 °C

7: 4A MS, DBU / CH₂Cl₂ / 0.25 h / 0 °C

8: 4A MS, trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / -30 °C

9: 1.) DBU, tris(triphenylphosphine)rhodium(I) chloride, 2.) HgCl₂ / 1.) ethanol, benzene, water, reflux, 24 h, 2.) acetone, H₂O, 20 deg C, 3 h

10: 84 percent / 4A MS, DBU / CH₂Cl₂ / 0.25 h / 0 °C

11: 1.) 4A MS, trimethylsilyl triflate, 2.) methylamine / 1.) CH₂Cl₂, 0 deg C, 30 min; 20 deg C, 10 min, 2.) EtOH, H₂O, room temperature, 48 h, 3.) CH₃OH, -10 deg C, 16 h

12: 92 percent / H₂ / Pd on charcoal / 96 h / 2844.3 Torr

With barium dihydroxide; potassium hydroxide; Wilkinson's catalyst; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; methylamine; mercury dichloride; barium(II) oxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; acetone;

Reference yield:

allyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (165874-22-6) → (1S,5S)-3-dimethylamino-8-exo-hydroxymethyl-7-endo-hydroxy-2-oxa-4-azabicyclo<3.3.0>oct-3-en-6-endo-yl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-allopyranosyl)-2-deoxy-β-D-allopyranoside (158528-74-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) KOH / 1.) CH₃OH, H₂O, 125 deg C, 5 d, 2.) CHCl₃, 20 deg C, 20 min

2: 89 percent / 2)2>PF₆ / tetrahydrofuran / 1.5 h

3: 91 percent / HgCl₂ / acetone; H₂O / 3 h / 20 °C

4: 4A MS, DBU / CH₂Cl₂ / 0.25 h / 0 °C

5: 4A MS, trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / -30 °C

6: 1.) DBU, tris(triphenylphosphine)rhodium(I) chloride, 2.) HgCl₂ / 1.) ethanol, benzene, water, reflux, 24 h, 2.) acetone, H₂O, 20 deg C, 3 h

7: 84 percent / 4A MS, DBU / CH₂Cl₂ / 0.25 h / 0 °C

8: 1.) 4A MS, trimethylsilyl triflate, 2.) methylamine / 1.) CH₂Cl₂, 0 deg C, 30 min; 20 deg C, 10 min, 2.) EtOH, H₂O, room temperature, 48 h, 3.) CH₃OH, -10 deg C, 16 h

9: 92 percent / H₂ / Pd on charcoal / 96 h / 2844.3 Torr

With potassium hydroxide; Wilkinson's catalyst; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; methylamine; mercury dichloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetone;

upstream raw materials:

allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

(1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene

(3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene

Refernces