METHYL 5,7,8,9-TETRA-O-ACETYL-4-ACYLAMINO-2,6-ANHYDRO-3,4-DIDEOXY-D-GLYCERO-D-GALACTO-2-ENONATE

Base Information

• Chemical Name: METHYL 5,7,8,9-TETRA-O-ACETYL-4-ACYLAMINO-2,6-ANHYDRO-3,4-DIDEOXY-D-GLYCERO-D-GALACTO-2-ENONATE
• CAS No.: 173467-18-0
• Molecular Formula: C₂₀H₂₇NO₁₂
• Molecular Weight: 473.434
• Mol file: 173467-18-0.mol

Synonyms:METHYL 5,7,8,9-TETRA-O-ACETYL-4-ACYLAMINO-2,6-ANHYDRO-3,4-DIDEOXY-D-GLYCERO-D-GALACTO-2-ENONATE;4-(AcetylaMino)-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonic Acid Methyl Ester 5,7,8,9-Tetraacetate

Chemical Property of METHYL 5,7,8,9-TETRA-O-ACETYL-4-ACYLAMINO-2,6-ANHYDRO-3,4-DIDEOXY-D-GLYCERO-D-GALACTO-2-ENONATE

Chemical Property:

• PSA: 173.32000
• LogP: 0.14530
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

Methyl 5,7,8,9-Tetra-O-acetyl-4-acylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-2-enonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 5,7,8,9-Tetra-O-acetyl-4-acylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-2-enonate (cas# 173467-18-0) is a compound useful in organic synthesis.

Technology Process of METHYL 5,7,8,9-TETRA-O-ACETYL-4-ACYLAMINO-2,6-ANHYDRO-3,4-DIDEOXY-D-GLYCERO-D-GALACTO-2-ENONATE

There total 4 articles about METHYL 5,7,8,9-TETRA-O-ACETYL-4-ACYLAMINO-2,6-ANHYDRO-3,4-DIDEOXY-D-GLYCERO-D-GALACTO-2-ENONATE 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: 16.0%

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate (123843-50-5) → α-(methoxycarbonyl)-furfuryl carbinol acetate (173467-17-9) + methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-talo-non-2-enonate (173467-19-1) + methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate (173467-18-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1248/cpb.43.1654

Reference yield: 16.0%

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate (123843-50-5) + acetonitrile (75-05-8,26809-02-9) → α-(methoxycarbonyl)-furfuryl carbinol acetate (173467-17-9) + methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-talo-non-2-enonate (173467-19-1) + methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate (173467-18-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; for 3h; Ambient temperature;

DOI:10.1248/cpb.43.1654

Reference yield:

methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (139110-77-3) → methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate (173467-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / 1 h / 50 °C

2: Me₃SiOTf / 3 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; In pyridine; 1: Elimination / 2: Ritter reaction;

DOI:10.1016/S0008-6215(99)00236-0

upstream raw materials:

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate

acetonitrile

methyl 4,5,7,8,9-penta-O-acetyl-2,3,5-trideoxy-D-glycero-D-galacto-non-2-eno-pyranosonate

methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Downstream raw materials:

4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonic acid

4-amino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonic acid

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