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

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-D-glycero-D-allo-heptafuranosiduronic acid
• CAS No.: 374556-99-7
• Molecular Formula: C₃₂H₄₈N₂O₉Si
• Molecular Weight: 632.827
• Mol file: 374556-99-7.mol

Synonyms: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

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-D-glycero-D-allo-heptafuranosiduronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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-D-glycero-D-allo-heptafuranosiduronic acid

There total 7 articles about 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 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%

methyl 6-deoxy-2,3-O-isopropylidene-6-(methylamino)-β-D-glycero-D-allo-heptafuranosiduronic acid (201933-47-3) + (2R,3R)-3-azido-4-(tert-butyldiphenylsilyloxy)-1,2-epoxybutane (201933-46-2) → 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)

Guidance literature:

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

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

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

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 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

With di-isopropyl azodicarboxylate; triphenylphosphine; trifluoroacetic acid; sodium t-butanolate; In tetrahydrofuran; 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-(methylamino)-β-D-glycero-D-allo-heptafuranosiduronic acid

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

(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

Downstream raw materials:

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