methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

Base Information

Chemical Name:methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate
CAS No.:1437796-22-9
Molecular Formula:C₂₅H₃₀FNO₁₂
Molecular Weight:555.511
Hs Code.:

Synonyms:methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

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Chemical Property of methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

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Technology Process of methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

There total 8 articles about methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate 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: 80.0%

: 1437796-21-8
methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5-dideoxy-3-fluoro-8-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate

: 1437796-22-9
methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

Guidance literature:: With 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; tri-n-butyl-tin hydride; In 1,4-dioxane; at 100 ℃; for 4h; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.carres.2013.03.026

Reference yield:

: 14131-64-7
N-acetyl-D-mannosamine

: 1437796-22-9
methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: N-acetylneuraminic aldolase / water / 120 h / 20 °C / Enzymatic reaction

1.2: dowex 1x2 200 ion exchange resin

2.1: trifluoroacetic acid / 16 h / 20 °C

3.1: triethylamine; toluene-4-sulfonic acid / acetone / 4 h / 20 °C

4.1: pyridine / 168 h / 4 - 20 °C

5.1: acetic acid / water / 2 h / 60 °C

6.1: pyridine / 7 h / 0 - 20 °C

7.1: pyridine / dichloromethane / 15 h / 0 - 20 °C

8.1: tri-n-butyl-tin hydride; 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; N-acetylneuraminic aldolase; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; acetone; 7.1: |Barton-McCombie Deoxygenation / 8.1: |Barton-McCombie Deoxygenation;
DOI:10.1016/j.carres.2013.03.026

Reference yield:

: 1214912-85-2
methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-D-erythro-α-L-manno-non-2-ulopyranosonate

: 1437796-22-9
methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 168 h / 4 - 20 °C

2: acetic acid / water / 2 h / 60 °C

3: pyridine / 7 h / 0 - 20 °C

4: pyridine / dichloromethane / 15 h / 0 - 20 °C

5: tri-n-butyl-tin hydride; 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; tri-n-butyl-tin hydride; acetic acid; In 1,4-dioxane; dichloromethane; water; 4: |Barton-McCombie Deoxygenation / 5: |Barton-McCombie Deoxygenation;
DOI:10.1016/j.carres.2013.03.026