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

Base Information

Chemical Name:allyl 4,6-O-benzylidene-2-deoxy-3-O-(4-methoxyphenylmethyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
CAS No.:206272-20-0
Molecular Formula:C₂₇H₃₀Cl₃NO₈
Molecular Weight:602.896
Hs Code.:

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

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

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

There total 1 articles about allyl 4,6-O-benzylidene-2-deoxy-3-O-(4-methoxyphenylmethyl)-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: 70.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

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

: 206272-20-0
allyl 4,6-O-benzylidene-2-deoxy-3-O-(4-methoxyphenylmethyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With tin(II) trifluoromethanesulfonate; In diethyl ether; at -20 - 0 ℃; for 2h;
DOI:10.1016/S0040-4020(98)00133-1

Reference yield:

: 206272-20-0
allyl 4,6-O-benzylidene-2-deoxy-3-O-(4-methoxyphenylmethyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 952429-82-2
[(2S,3R,4R,5S,6R)-2-Allyloxy-5-benzyloxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

Guidance literature:: With dimethylamine borane; boron trifluoride diethyl etherate; In dichloromethane; at -40 - 0 ℃; for 2h;
DOI:10.1016/S0040-4020(98)00133-1

Reference yield:

: 206272-20-0
allyl 4,6-O-benzylidene-2-deoxy-3-O-(4-methoxyphenylmethyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 206272-23-3
C₆₀H₇₃Cl₆N₂O₁₈P

Guidance literature:: Multi-step reaction with 5 steps

1: BH₃*Me₂NH; BF₃*Et₂O / CH₂Cl₂ / 2 h / -40 - 0 °C

2: 325 mg / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

3: 91 percent / molecular sieves 4A; trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / -20 °C

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

5: 85 percent / n-BuNH₂; HCOOH / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 20 °C

With dmap; formic acid; trimethylsilyl trifluoromethanesulfonate; dimethylamine borane; 4 A molecular sieve; boron trifluoride diethyl etherate; N-butylamine; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1: Ring cleavage / 2: dealkylation / 3: Condensation / 4: Acylation / 5: deprotection;
DOI:10.1016/S0040-4020(98)00133-1