allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Base Information

Chemical Name:allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside
CAS No.:828939-76-0
Molecular Formula:C₅₇H₉₃NO₈
Molecular Weight:920.367
Hs Code.:

Synonyms:allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

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Chemical Property of allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

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Technology Process of allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

There total 5 articles about allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-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: 85.0%

: 828939-42-0
(R)-3-(benzyloxy)icosanoic acid

: 828939-74-8
allyl 2-amino-4-O-benzyl-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

: 828939-76-0
allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; chloroform; for 1h;
DOI:10.1016/j.tet.2004.10.017

Reference yield:

: 14531-35-2
methyl 3-oxoicosanoate

: 828939-76-0
allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / hydrogen; (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-RuCl₂ / methanol / 44 h / 60 °C / 64600 Torr

2: 90 percent / hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate; triethylsilane / tetrahydrofuran / 0 - 20 °C

3: 90 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 3 h / Heating

4: 85 percent / 1-hydroxy-benzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂; CHCl₃ / 1 h

With triethylsilane; lithium hydroxide; dichloro-R-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ruthenium; Hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 1: Noyori hydrogenation;
DOI:10.1016/j.tet.2004.10.017

Reference yield:

: 136890-22-7
(R)-β-hydroxyeicosanoic acid methyl ester

: 828939-76-0
allyl 4-O-benzyl-2-[(R)-3-(benzyloxy)icosanoylamino]-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate; triethylsilane / tetrahydrofuran / 0 - 20 °C

2: 90 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 3 h / Heating

3: 85 percent / 1-hydroxy-benzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂; CHCl₃ / 1 h

With triethylsilane; lithium hydroxide; Hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; chloroform; water;
DOI:10.1016/j.tet.2004.10.017