5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:219703-39-6
Molecular Formula:C₂₅H₂₈N₄O₈
Molecular Weight:512.519
Hs Code.:

Synonyms:5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of 5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of 5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 3 articles about 5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-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: 63.0%

: 100-39-0
benzyl bromide

: 243136-75-6
2-{(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

: 219703-39-6
5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: With tetrabutylammomium bromide; bis(tri-n-butyltin)oxide; In toluene; at 100 ℃; for 4h;
DOI:10.1016/S0008-6215(99)00022-1

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 219703-39-6
5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / SnCl₄ / CH₂Cl₂ / 20 °C

2: 96 percent / sodium methoxide / methanol; CH₂Cl₂ / 0.5 h

3: 63 percent / bis(tri-n-butyl)tin oxide; tetrabutylammonium bromide / toluene / 4 h / 100 °C

With tetrabutylammomium bromide; sodium methylate; tin(IV) chloride; bis(tri-n-butyltin)oxide; In methanol; dichloromethane; toluene; 1: Condensation / 2: deprotection / 3: Etherification;
DOI:10.1016/S0008-6215(99)00022-1

Reference yield:

: 243136-74-5
5-azido-3-oxapentyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 219703-39-6
5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / sodium methoxide / methanol; CH₂Cl₂ / 0.5 h

2: 63 percent / bis(tri-n-butyl)tin oxide; tetrabutylammonium bromide / toluene / 4 h / 100 °C

With tetrabutylammomium bromide; sodium methylate; bis(tri-n-butyltin)oxide; In methanol; dichloromethane; toluene; 1: deprotection / 2: Etherification;
DOI:10.1016/S0008-6215(99)00022-1