allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• CAS No.: 206272-11-9
• Molecular Formula: C₂₃H₂₆Cl₃NO₉
• Molecular Weight: 566.82
• Mol file: 206272-11-9.mol

Synonyms:allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property of allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 1 articles about allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 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: 66.0%

Allyl chloroformate (2937-50-0) + allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside → allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-11-9)

Guidance literature:

With pyridine; dmap; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1016/S0040-4020(98)00133-1

Reference yield: 90.0%

allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-11-9) → allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-12-0)

Guidance literature:

With dimethylamine borane; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4020(98)00133-1

Reference yield:

allyl 3-O-allyloxycarbonyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (206272-11-9) → C64H77Cl6N2O20P (206272-22-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / BH₃*Me₂NH; BF₃*Et₂O / acetonitrile / 1.5 h / 0 °C

2: 1H-tetrazole / 1,2-dichloro-ethane / 0.25 h / 20 °C

3: 3.24 g / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 0.33 h / -20 °C

4: hydrogen / [Ir(cod)(PPh₂Me)2]PF₆ / tetrahydrofuran / 14 h / 20 °C

5: 482 mg / iodine / tetrahydrofuran; H₂O / 1 h

6: 97 percent / molecular sieves 4A; Cs₂CO₃ / 1,2-dichloro-ethane / 1.25 h / 20 °C

7: 91 percent / molecular sieves 4A; trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / -20 °C

8: 98 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 1 h / 20 °C

With 1H-tetrazole; dmap; trimethylsilyl trifluoromethanesulfonate; dimethylamine borane; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; iodine; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; water; 1,2-dichloro-ethane; acetonitrile; 1: Ring cleavage / 2: phosphitylation / 3: Oxidation / 4: Isomerization / 5: Hydrolysis / 6: Addition / 7: Condensation / 8: Acylation;

DOI:10.1016/S0040-4020(98)00133-1

upstream raw materials:

Allyl chloroformate

Downstream raw materials:

allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

allyl 6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-4-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside