3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate
• CAS No.: 1334371-19-5
• Molecular Formula: C₃₃H₃₇NO₁₀
• Molecular Weight: 607.657
• Mol file: 1334371-19-5.mol

Synonyms:3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate

Chemical Property of 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate

There total 1 articles about 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate 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: 83.0%

3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-D-glucopyranose (129729-40-4,130005-73-1) + 2-(1-hexyn-1-yl)benzoic acid (120870-47-5) → 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate (1334371-19-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/anie.201103409

Reference yield: 91.0%

triphenylphosphinegold(I) triflate + 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate (1334371-19-5) → [(C6H5)3PAu(C9H4O(O)CH2CH2CH2CH3)]

Guidance literature:

With CH₂CH(CH₂)3OH; In toluene; byproducts: (CH3COO)2C5H5O(CH2OCOCH3)(NCHC6H4OCH3)(OC3H6CHCH2), (CH3COO)2C5H5O(CH2OCOCH3)(NH2)(OC3H6CHCH2); at room temp. for 4 h; flash chromy. on silica gel;

DOI:10.1002/anie.201103409

Reference yield: 37.0%

n-Pent-4-enyl alcohol (821-09-0) + trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) (156397-47-6) + 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl ortho-hexynylbenzoate (1334371-19-5) → [(C6H5)3PAu(C9H4O(O)CH2CH2CH2CH3)] + n-pentenyl 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranoside (1334371-23-1) + n-pentenyl 3,4,6-tri-O-acetyl-2-deoxy-2-amino-α-D-glucopyranoside

Guidance literature:

In toluene; at 20 ℃; for 4h; Molecular sieve;

DOI:10.1002/anie.201103409

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-D-glucopyranose

2-(1-hexyn-1-yl)benzoic acid

Downstream raw materials:

n-pentenyl 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranoside