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

Base Information

Chemical Name:allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:206272-12-0
Molecular Formula:C₂₃H₂₈Cl₃NO₉
Molecular Weight:568.836
Hs Code.:

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

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

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

There total 2 articles about allyl 3-O-allyloxycarbonyl-6-O-benzyl-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: 90.0%

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

: 206272-12-0
allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

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

: 206272-12-0
allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / pyridine; DMAP / 1,2-dichloro-ethane / 1.5 h / 0 - 20 °C

2: 90 percent / BH₃*Me₂NH; BF₃*Et₂O / acetonitrile / 1.5 h / 0 °C

With pyridine; dmap; dimethylamine borane; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; acetonitrile; 1: Acylation / 2: Ring cleavage;
DOI:10.1016/S0040-4020(98)00133-1

Reference yield:

: 206272-12-0
allyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 206272-19-7
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

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

4: 482 mg / iodine / tetrahydrofuran; H₂O / 1 h

5: 97 percent / molecular sieves 4A; Cs₂CO₃ / 1,2-dichloro-ethane / 1.25 h / 20 °C

With 1H-tetrazole; 4 A molecular sieve; hydrogen; iodine; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; water; 1,2-dichloro-ethane; 1: phosphitylation / 2: Oxidation / 3: Isomerization / 4: Hydrolysis / 5: Addition;
DOI:10.1016/S0040-4020(98)00133-1