Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

Base Information

• Chemical Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside
• CAS No.: 99409-32-2
• Molecular Formula: C22H25NO9S
• Molecular Weight: 479.508
• Hs Code.: 2938909090
• Mol file: 99409-32-2.mol

Synonyms:Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside;Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-thioglucopyranoside;Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside

Chemical Property of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

Chemical Property:

• PSA: 150.81000
• LogP: 1.49360
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl 3,4,6-tri-O-Acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside is a reactant in the synthesis of Me 2-amino-2-deoxy-α-D-glucopyranoside 6-phosphate, Me 2-amino-2-deoxy-β-D-glucopyranoside 6-phosphate as cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU.

Technology Process of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside

There total 20 articles about Ethyl 3,4,6-tri-O-acetyl-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: 99.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + ethanethiol (75-08-1) → ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 7 - 8 ℃; for 168h;

DOI:10.1016/S0008-6215(96)00235-2

Reference yield: 96.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) + ethanethiol (75-08-1) → ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.75h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1039/c9ob01610d

Reference yield: 92.0%

2-deoxy-2-phthalimido-D-glucopyranose (31505-45-0) + acetic anhydride (108-24-7) + ethanethiol (75-08-1) → ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2)

Guidance literature:

2-deoxy-2-phthalimido-D-glucopyranose; acetic anhydride; With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

ethanethiol; With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1002/ejoc.200500646

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

ethanethiol

1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside

1,2,3,4-tetra-O-benzoyl-6-O-(3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranose