allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
CAS No.:219795-86-5
Molecular Formula:C₄₁H₄₈N₂O₁₁
Molecular Weight:744.839
Hs Code.:

allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Synonyms:allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 9 articles about allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-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:

: 120142-50-9
allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 219795-86-5
allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dioxane; paraffin / 18 h / 70 °C

2: Ac₂O, pyridine, Dovex H⁽¹⁺⁾ / 24 h / 20 °C

3: diethyl ether; CHCl₃; methanol / 0 °C

4: 74 percent / 1,8-diazabicyclo<2.2.2>octane / tris(trophenylphosphine)rhodium(I) chloride / ethanol; benzene; diethyl ether / 30 h / Heating

5: 82 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

6: 66 percent / Me₃SiOTf / CH₂Cl₂ / 20 °C

7: 77 percent / LiI / pyridine / 20 h / 107 °C

8: 1.) ethylenediamine; 2.) pyridine / 1.) n-butanol, 100 deg C, 20 h; 2.) r.t., overnight

With pyridine; 1,8-diazabicyclo[2.2.2.]octane; trimethylsilyl trifluoromethanesulfonate; Dovex H⁽¹⁺⁾; acetic anhydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; lithium iodide; Wilkinson's catalyst; In 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; paraffin; benzene;
DOI:10.1016/S0008-6215(98)00248-1

Reference yield:

: 219795-79-6
(R)-2-[(2R,4aR,6R,7R,8R,8aS)-6-Allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid

: 219795-86-5
allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: diethyl ether; CHCl₃; methanol / 0 °C

2: 74 percent / 1,8-diazabicyclo<2.2.2>octane / tris(trophenylphosphine)rhodium(I) chloride / ethanol; benzene; diethyl ether / 30 h / Heating

3: 82 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

4: 66 percent / Me₃SiOTf / CH₂Cl₂ / 20 °C

5: 77 percent / LiI / pyridine / 20 h / 107 °C

6: 1.) ethylenediamine; 2.) pyridine / 1.) n-butanol, 100 deg C, 20 h; 2.) r.t., overnight

With pyridine; 1,8-diazabicyclo[2.2.2.]octane; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; lithium iodide; Wilkinson's catalyst; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; benzene;
DOI:10.1016/S0008-6215(98)00248-1

Reference yield:

: 219795-77-4
(R)-2-[(2R,4aR,6R,7R,8R,8aS)-6-Allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid methyl ester

: 219795-86-5
allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-D-glucopyranosyl-1',2-lactam)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / 1,8-diazabicyclo<2.2.2>octane / tris(trophenylphosphine)rhodium(I) chloride / ethanol; benzene; diethyl ether / 30 h / Heating

2: 82 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

3: 66 percent / Me₃SiOTf / CH₂Cl₂ / 20 °C

4: 77 percent / LiI / pyridine / 20 h / 107 °C

5: 1.) ethylenediamine; 2.) pyridine / 1.) n-butanol, 100 deg C, 20 h; 2.) r.t., overnight

With pyridine; 1,8-diazabicyclo[2.2.2.]octane; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; lithium iodide; Wilkinson's catalyst; In pyridine; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1016/S0008-6215(98)00248-1