(1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Base Information

• Chemical Name: (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol
• CAS No.: 364046-26-4
• Molecular Formula: C₃₀H₄₃N₃O₅Si
• Molecular Weight: 553.774
• Mol file: 364046-26-4.mol

Synonyms:(1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Chemical Property of (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

There total 7 articles about (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 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: 69.0%

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-33-9) + 1-N-benzyloxymethyl-3-bromo-7-methoxypyrrolo[2,3-c]pyridine (364046-09-3) → (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (364046-26-4)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; methoxybenzene; at -70 - 20 ℃;

DOI:10.1021/jo0155613

Reference yield:

2-chloro-3-nitro-4-methylpyridine (23056-39-5) → (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (364046-26-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / methanol / 2 h / Heating

2: 99 percent / dimethylformamide / 18 h / 130 °C

3: 89 percent / H₂ / Pd/C / ethanol / 0.25 h / 775.74 Torr

4: 72 percent / NaH / tetrahydrofuran / 2 h / 20 °C

5: 74 percent / Br₂ / CHCl₃

6: 69 percent / n-BuLi / methoxybenzene; diethyl ether; hexane / -70 - 20 °C

With n-butyllithium; hydrogen; bromine; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; chloroform; methoxybenzene; N,N-dimethyl-formamide;

DOI:10.1021/jo0155613

Reference yield:

2-methoxy-4-methyl-3-nitropyridine (160590-36-3) → (1S)-1-(1-N-benzyloxymethyl-7-methoxypyrrolo[2,3-c]pyridin-3-yl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (364046-26-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / dimethylformamide / 18 h / 130 °C

2: 89 percent / H₂ / Pd/C / ethanol / 0.25 h / 775.74 Torr

3: 72 percent / NaH / tetrahydrofuran / 2 h / 20 °C

4: 74 percent / Br₂ / CHCl₃

5: 69 percent / n-BuLi / methoxybenzene; diethyl ether; hexane / -70 - 20 °C

With n-butyllithium; hydrogen; bromine; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; chloroform; methoxybenzene; N,N-dimethyl-formamide;

DOI:10.1021/jo0155613

upstream raw materials:

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

1-N-benzyloxymethyl-3-bromo-7-methoxypyrrolo[2,3-c]pyridine

Benzyloxymethyl chloride

2-chloro-3-nitro-4-methylpyridine