5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Base Information

• Chemical Name: 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol
• CAS No.: 433217-46-0
• Molecular Formula: C₂₈H₃₆N₄O₇
• Molecular Weight: 541.608
• Mol file: 433217-46-0.mol

Synonyms:5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Chemical Property of 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-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 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

There total 3 articles about 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-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: 91.0%

5-aldehydo-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (433217-45-9) → 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (433217-46-0)

Guidance literature:

With sodium borodeuteride; In deuteromethanol; for 1h;

DOI:10.1002/jlcr.533

Reference yield:

1S-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-C-[(4-methyoxypyrrolo[3,2-d]pyrimidin-9-N-(benzyloxomethyl)-7-yl)]-1,4-imino-2,3-O-isopropylidine-D-ribitol (364046-19-5) → 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (433217-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h

2: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h

3: 91 percent / NaB[2H]4 / CH₃OD / 1 h

With sodium borodeuteride; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; deuteromethanol; 2: Dess-Martin oxidation;

DOI:10.1002/jlcr.533

Reference yield:

(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (433217-44-8) → 5-[2H]-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (433217-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h

2: 91 percent / NaB[2H]4 / CH₃OD / 1 h

With sodium borodeuteride; Dess-Martin periodane; In dichloromethane; deuteromethanol; 1: Dess-Martin oxidation;

DOI:10.1002/jlcr.533

upstream raw materials:

5-aldehydo-(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

1S-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-C-[(4-methyoxypyrrolo[3,2-d]pyrimidin-9-N-(benzyloxomethyl)-7-yl)]-1,4-imino-2,3-O-isopropylidine-D-ribitol

(1S)-1-C-(5-N-benzyloxymethyl-4-methoxypyrrolo[3,2-d]pyrimidin-7-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol