N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 1334540-16-7
• Molecular Formula: C₄₇H₅₃NO₈
• Molecular Weight: 759.94

Synonyms:N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

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Technology Process of N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

There total 2 articles about N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-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:

C58H61NO8 → N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (1334540-16-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 2h;

DOI:10.1039/c1cc13614c

Reference yield:

benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester (920958-49-2) + ethyl 3,4,6-tri-O-benzyl-2-O-(2-naphthalenylmethyl)-1-thio-D-glucopyranoside (1334540-30-5) → N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (1334540-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / 1,4-dioxane; toluene / 1.5 h / -40 - -20 °C

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1039/c1cc13614c

Reference yield: 70.0%

N-(benzyl)benzyloxycarbonyl-5-amino-pentanyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (1334540-16-7) + S-(2-methyl-5-tert-butylphenyl)-2,6-di-O-benzyl-3-O-fluorenyl-methoxycarbonyl-4-O-levulinoyl-1-thio-β-D-glucopyranoside (1334540-18-9) → 2,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-4-O-levulinoyl-α-D-glucopyranosyl-(1→2)-(N-(benzyl)-N-benzyloxycarbonyl-5-amino-pentyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside (1334540-61-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; at -35 - -10 ℃; for 1h; Inert atmosphere;

upstream raw materials:

benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester

ethyl 3,4,6-tri-O-benzyl-2-O-(2-naphthalenylmethyl)-1-thio-D-glucopyranoside

Downstream raw materials:

2,6-di-O-benzyl-3-O-fluorenylmethoxycarbonyl-4-O-levulinoyl-α-D-glucopyranosyl-(1→2)-(N-(benzyl)-N-benzyloxycarbonyl-5-amino-pentyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

N-(benzyl)benzyloxycarbonyl-5-aminopentanyl 2,6-di-O-benzyl-3-O-(4-bromobenzyl)-4-O-levulinoyl-α-D-glucopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

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