methyl (5R)-5-C-[(2'R,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 (5R)-5-C-[(2'R,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.: 374557-00-3
• Molecular Formula: C₃₂H₄₆N₂O₈Si
• Molecular Weight: 614.811
• Mol file: 374557-00-3.mol

Synonyms:methyl (5R)-5-C-[(2'R,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

Chemical Property of methyl (5R)-5-C-[(2'R,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (5R)-5-C-[(2'R,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 9 articles about methyl (5R)-5-C-[(2'R,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: 34.0%

methyl 6-deoxy-2,3-O-isopropylidene-6-{methyl[(2'S,3'R)-3'-amino-4'-(tert-butyldiphenylsilyloxy)-2'-hydroxybutyl]amino}-β-D-glycero-D-allo-heptafuranosiduronic acid (374556-99-7) → methyl (5R)-5-C-[(2'R,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 (374557-00-3)

Guidance literature:

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

DOI:10.1002/1099-0690(200108)2001:16<3089::AID-EJOC3089>3.0.CO;2-L

Reference yield:

(S)-4-{(1S)-2-[(1,1-dimethylethyl)diphenylsilyloxy]-1-(hydroxy)ethyl}-2,2-dimethyl-1,3-dioxolane (183888-74-6) → methyl (5R)-5-C-[(2'R,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 (374557-00-3)

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:

(2R,3R)-3-azido-4-tert-butyldiphenylsilyloxy-1,2-O-isopropylidenebutane-1,2-diol (201933-48-4) → methyl (5R)-5-C-[(2'R,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 (374557-00-3)

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

upstream raw materials:

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

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

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

methyl 6-deoxy-2,3-O-isopropylidene-6-(methylamino)-β-D-glycero-D-allo-heptafuranosiduronic acid