methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

Base Information

Chemical Name:methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid
CAS No.:201933-51-9
Molecular Formula:C₃₂H₄₈N₂O₉Si
Molecular Weight:632.827
Hs Code.:

methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

Synonyms:methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

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Chemical Property of methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

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Technology Process of methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

There total 18 articles about methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid 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: 65.0%

: 201933-55-3
methyl 6-deoxy-2,3-O-isopropylidene-6-(methylamino)-L-glycero-L-talo-heptafuranosiduronic acid

: 201933-46-2
(2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane

: 201933-51-9
methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

Guidance literature:: methyl 6-deoxy-2,3-O-isopropylidene-6-(methylamino)-L-glycero-L-talo-heptafuranosiduronic acid; (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane; With sodium t-butanolate; In tert-butyl alcohol; at 100 ℃; for 48h;

With hydrogen; 10% palladium on active carbon; In methanol;
DOI:10.1002/1099-0690(200108)2001:16<3089::AID-EJOC3089>3.0.CO;2-L

Reference yield: 65.0%

: (2S,3S)-2-{[(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl]-methyl-amino}-3-hydroxy-3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid

: 201933-51-9
methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol;
DOI:10.1016/S0040-4039(97)10597-4

Reference yield:

: 183888-74-6
(S)-4-{(1S)-2-[(1,1-dimethylethyl)diphenylsilyloxy]-1-(hydroxy)ethyl}-2,2-dimethyl-1,3-dioxolane

: 201933-51-9
methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-L-glycero-L-talo-heptafuranosiduronic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 81 percent / tetramethylguanidinium azide / CH₂Cl₂ / -78 - 20 °C

3.1: 65 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 2 h / 0 °C

4.1: 79 percent / triphenylphosphane; diisopropyl azodicarboxylate / toluene / 2.5 h / 130 °C / 0.01 Torr

5.1: sodium tert-butoxide / 2-methyl-propan-2-ol / 48 h / 100 °C

5.2: 65 percent / H₂ / 10 percentPd/C / methanol

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; triphenylphosphine; tetramethylguanidinum azide; trifluoroacetic acid; sodium t-butanolate; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: Mitsunobu reaction;
DOI:10.1002/1099-0690(200108)2001:16<3089::AID-EJOC3089>3.0.CO;2-L