3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene

Base Information

• Chemical Name: 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene
• CAS No.: 1385808-92-3
• Molecular Formula: C₄₇H₅₁N₅O₈S
• Molecular Weight: 846.017
• Mol file: 1385808-92-3.mol

Synonyms:3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene

Chemical Property of 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene

There total 6 articles about 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene 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: 93.0%

3-[6-O-(2-azido)acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]prop-1-ene (1385808-90-1) + 5-(dimethylamino)-N-(prop-2-yn-1-yl)naphthalene-1-sulfonamide (175728-78-6) → 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene (1385808-92-3)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; at 20 ℃; optical yield given as %de;

DOI:10.1055/s-0031-1290975

Reference yield:

C32H35ClO6 → 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene (1385808-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide; potassium iodide / acetone / 24 h / 20 °C

2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / dichloromethane / 20 °C

With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium iodide; In dichloromethane; acetone; 2: Huisgen cycloaddition;

DOI:10.1055/s-0031-1290975

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → 3-{2,3,4-tri-O-benzyl-6-O-{4-[(5-dimethylaminonaphthalene-1-sulfonylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl-α-D-glucopyranosyl}prop-1-ene (1385808-92-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 14 h / 0 - 20 °C

2: sodium azide; potassium iodide / acetone / 24 h / 20 °C

3: trimethylsilyl trifluoromethanesulfonate / acetonitrile

4: copper(ll) sulfate pentahydrate; sodium L-ascorbate / dichloromethane / 20 °C

With sodium azide; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; sodium L-ascorbate; triethylamine; potassium iodide; In dichloromethane; acetone; acetonitrile; 4: Huisgen cycloaddition;

DOI:10.1055/s-0031-1290975

upstream raw materials:

3-[6-O-(2-azido)acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl]prop-1-ene

5-(dimethylamino)-N-(prop-2-yn-1-yl)naphthalene-1-sulfonamide

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-α-D-glucopyranoside