methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

Base Information

Chemical Name:methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside
CAS No.:201933-52-0
Molecular Formula:C₃₂H₄₆N₂O₈Si
Molecular Weight:614.811
Hs Code.:

methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

Synonyms:methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

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Chemical Property of methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

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Technology Process of methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

There total 19 articles about methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside 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: 35.0%

: 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

: 201933-52-0
methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 15h;
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

: 201933-52-0
methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 6 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

6.1: 34 percent / dicyclohexyl carbodiimide / CH₂Cl₂ / 15 h / 0 °C

With 2,6-dimethylpyridine; di-isopropyl azodicarboxylate; dicyclohexyl-carbodiimide; 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

Reference yield:

: 201933-48-4
(2R,3R)-3-azido-4-tert-butyldiphenylsilyloxy-1,2-O-isopropylidenebutane-1,2-diol

: 201933-52-0
methyl (5S)-5-C-[(2'S,5'R,6'S)-5'-(tert-butyldiphenylsilyloxymethyl)-6'-hydroxy-1'-methyl-3'-oxo-1',4'-diazepan-2'-yl]-5-hydroxy-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 65 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 2 h / 0 °C

2.1: 79 percent / triphenylphosphane; diisopropyl azodicarboxylate / toluene / 2.5 h / 130 °C / 0.01 Torr

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

3.2: 65 percent / H₂ / 10 percentPd/C / methanol

4.1: 34 percent / dicyclohexyl carbodiimide / CH₂Cl₂ / 15 h / 0 °C

With di-isopropyl azodicarboxylate; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; sodium t-butanolate; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 2.1: Mitsunobu reaction;
DOI:10.1002/1099-0690(200108)2001:16<3089::AID-EJOC3089>3.0.CO;2-L