N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

Base Information

Chemical Name:N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose
CAS No.:1419313-61-3
Molecular Formula:C₁₃H₁₅NO₄S
Molecular Weight:281.332
Hs Code.:

Synonyms:N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

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Chemical Property of N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

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Technology Process of N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

There total 4 articles about N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose 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: 68.0%

: 75556-27-3
2,3,4-Tri-O-acetyl-1,5-anhydro-6-deoxy-L-arabino-hex-1-enitol

: 70-55-3
toluene-4-sulfonamide

: 1419313-61-3
N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

: 1419313-63-5
C₁₃H₁₅NO₄S

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.333333h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jo302619b

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4
1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

: 1419313-61-3
N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

: 1419313-63-5
C₁₃H₁₅NO₄S

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogen bromide; acetic acid

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide

3: boron trifluoride diethyl etherate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; hydrogen bromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; 3: |Ferrier Carbohydrate Rearrangement;
DOI:10.1021/jo302619b

Reference yield:

: 69980-52-5
2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide

: 1419313-61-3
N-(p-methylphenylsulfonamido)-6-methyl-3,4-dideoxy-D-rhamnal-hex-3-eno-pyranoside-2-ulose

: 1419313-63-5
C₁₃H₁₅NO₄S

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide

2: boron trifluoride diethyl etherate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; 2: |Ferrier Carbohydrate Rearrangement;
DOI:10.1021/jo302619b