((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Base Information

• Chemical Name: ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester
• CAS No.: 854377-25-6
• Molecular Formula: C₃₉H₅₆N₄O₁₅
• Molecular Weight: 820.891
• Mol file: 854377-25-6.mol

Synonyms:((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Chemical Property of ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester

There total 3 articles about ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester 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: 83.0%

methyl (6'-amino-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-24-5) + (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid (854377-20-1) → ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester (854377-25-6)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0502899

Reference yield:

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid (854377-20-1) → ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester (854377-25-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.01 g / NaHCO₃ / dimethylformamide / 72 h

2: 98.5 percent / triphenylphosphine / tetrahydrofuran; H₂O / 48 h / 20 °C

3: 83 percent / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

With diethyl cyanophosphonate; sodium hydrogencarbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0502899

Reference yield:

methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-22-3) → ((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid methyl ester (854377-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98.5 percent / triphenylphosphine / tetrahydrofuran; H₂O / 48 h / 20 °C

2: 83 percent / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

With diethyl cyanophosphonate; triethylamine; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0502899

upstream raw materials:

methyl (6'-amino-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid

methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

Downstream raw materials:

C₅₈H₈₃N₅O₂₂

C₅₇H₈₁N₃O₂₁

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane