Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

Base Information

• Chemical Name: Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside
• CAS No.: 129519-28-4
• Molecular Formula: C23H23NO6S
• Molecular Weight: 441.505
• Mol file: 129519-28-4.mol

Synonyms:Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside;Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-1-thio-beta-D-glucopyranoside

Chemical Property of Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

Chemical Property:

• PSA: 112.37000
• LogP: 0.76790

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

There total 6 articles about Ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-thioglucopyranoside 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: 87.0%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4) → 2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃;

DOI:10.1016/S0960-894X(01)00550-9

Reference yield: 74.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + benzaldehyde dimethyl acetal (1125-88-8) + ethanethiol (75-08-1) → 2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4)

Guidance literature:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose; ethanethiol; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 40 ℃; for 19h; Molecular sieve;

With sodium methylate; In methanol; for 2h; pH=10;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 2.5h; pH=3;

Reference yield: 67.0%

ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4) + benzaldehyde (100-52-7) → 2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4)

Guidance literature:

With ytterbium(III) triflate; trimethyl orthoformate; In neat (no solvent); at 90 ℃; for 2.5h;

DOI:10.1002/adsc.201500745

upstream raw materials:

benzaldehyde dimethyl acetal

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

benzaldehyde

Downstream raw materials:

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Refernces

• 1、 -. "New monosaccharide derivatives and biological applications thereof". Paragraph 0043; 0044. . Retrieved 2014/01/07.
• 2、 Misra, Anup Kumar,Fukuda, Minoru,Hindsgaul, Ole. "Efficient synthesis of lactosaminylated core-2 O-glycans". . p. 2667 - 2669. Retrieved 2007/10/03.