(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol

Base Information

• Chemical Name: (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol
• CAS No.: 608530-17-2
• Molecular Formula: C₃₄H₃₅NO₁₀
• Molecular Weight: 617.653
• Mol file: 608530-17-2.mol

Synonyms:(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol

Chemical Property of (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol

There total 3 articles about (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol 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: 85.0%

(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-tert-butyldimethylsilyl-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol (608530-16-1) → (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol (608530-17-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/ejoc.200300255

Reference yield:

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde (256397-91-8) → (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol (608530-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 343 mg / MgBr₂; methyllithium / diethyl ether / -30 - 20 °C

2: 90 percent / DEAD; triphenylphosphane / tetrahydrofuran / 1 h / 0 °C

3: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

With tetrabutyl ammonium fluoride; methyllithium; triphenylphosphine; magnesium bromide; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether;

DOI:10.1002/ejoc.200300255

Reference yield:

(1S,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol (256397-92-9) → (1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol (608530-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / DEAD; triphenylphosphane / tetrahydrofuran / 1 h / 0 °C

2: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1002/ejoc.200300255

upstream raw materials:

(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-tert-butyldimethylsilyl-1-O-(4-nitrobenzoyl)pent-2-yne-1,4-diol

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde

(1S,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

Downstream raw materials:

methyl (3S,4E,6R)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-(2,4-dichlorobenzoyloxy)-2-(methoxycarbonyl)-3-methylhex-4-enoate

methyl (3S,4E,6R)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-(methoxycarbonyl)-3-methylhex-4-enoate

(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(ethoxycarbonyl)pent-2-yne-1,4-diol

(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(ethoxycarbonyl)pent-2-ene-1,4-diol