1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Base Information

• Chemical Name: 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione
• CAS No.: 174290-90-5
• Molecular Formula: C₅₇H₆₀N₄O₁₁Si
• Molecular Weight: 1005.21
• Mol file: 174290-90-5.mol

Synonyms:1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Chemical Property of 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione

There total 15 articles about 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione 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:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione (174290-90-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, RT, overnight

2: BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

3: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

4: 97 percent / NaH / CH₂Cl₂ / Ambient temperature

5: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) DMF, 30 min, 2.) DMF, 40 deg C, 10 h

6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

7: 1.) NaH / 1.) DMF, from 0 deg C to RT, 20 min, 2.) DMF, RT, 4 h

8: 3,3-dimethyldioxirane / CH₂Cl₂ / 0 °C

9: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, a) from 0 deg C to RT, 30 min, b) reflux, 1 h

With pyridine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja952907g

Reference yield:

3-amino-1,5-anhydro-2,3-dideoxy-3,O,4,N-<(trichloromethyl)oxazolino>-6-O-(triisopropylsilyl)-D-ribo-hex-1-enopyranose (148302-24-3) → 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione (174290-90-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

2: 97 percent / NaH / CH₂Cl₂ / Ambient temperature

3: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) DMF, 30 min, 2.) DMF, 40 deg C, 10 h

4: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

5: 1.) NaH / 1.) DMF, from 0 deg C to RT, 20 min, 2.) DMF, RT, 4 h

6: 3,3-dimethyldioxirane / CH₂Cl₂ / 0 °C

7: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, a) from 0 deg C to RT, 30 min, b) reflux, 1 h

With pyridine; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja952907g

Reference yield:

1,5-anhydro-2,3-dideoxy-3-(trichloroacetamido)-6-O-(triisopropylsilyl)-D-ribo-hex-1-enopyranose (148302-25-4) → 1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione (174290-90-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / NaH / CH₂Cl₂ / Ambient temperature

2: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) DMF, 30 min, 2.) DMF, 40 deg C, 10 h

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

4: 1.) NaH / 1.) DMF, from 0 deg C to RT, 20 min, 2.) DMF, RT, 4 h

5: 3,3-dimethyldioxirane / CH₂Cl₂ / 0 °C

6: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, a) from 0 deg C to RT, 30 min, b) reflux, 1 h

With tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja952907g

upstream raw materials:

1-<(benzyloxy)methyl>-3,4-dihydro-4-(1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione

indole

(2-trimethylethylsilylethoxy)methyl chloride

N-benzyloxymethyl-3,4-dibromomaleimide

Downstream raw materials:

1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-2-O-<(pentafluorophenoxy)thiocarbonyl>-α-D-altropyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dion