ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate

Base Information

• Chemical Name: ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate
• CAS No.: 631918-74-6
• Molecular Formula: C₃₀H₃₉NO₈
• Molecular Weight: 541.642
• Mol file: 631918-74-6.mol

Synonyms:ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate

Chemical Property of ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate

There total 1 articles about ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate 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: 93.0%

ethyl bromoacetate (105-36-2) + (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate (329361-79-7) → ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate (631918-74-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1016/S0968-0896(03)00231-1

Reference yield: 83.0%

ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate (631918-74-6) → 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-2-hydroxyethyl)amino-5,6-dideoxy-β-L-ido-heptofuranose (631918-76-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(03)00231-1

Reference yield:

ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-carbethoxymethyl)amino-5,6-dideoxy-β-L-ido-heptofuranuronate (631918-74-6) → Acetic acid (S)-3-[(2-acetoxy-ethyl)-benzyloxycarbonyl-amino]-3-((2R,3R,4R)-3,4,5-trihydroxy-tetrahydro-furan-2-yl)-propyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / LAH / tetrahydrofuran / 2 h / 20 °C

2: 82 percent / pyridine / 4 h / 0 - 20 °C

3: 71 percent / hydrogen / Pd/C / methanol / 12 h / 20 °C / 4137.18 Torr

4: 90 percent / NaHCO₃ / ethanol; H₂O / 3 h / 0 °C

5: TFA / H₂O / 0 - 30 °C

With pyridine; lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1016/S0968-0896(03)00231-1

upstream raw materials:

ethyl bromoacetate

(1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-β-L-ido-heptofurannuronate

Downstream raw materials:

1,2-O-isopropylidene-3-O-benzyl-5-(N-benzyl-N-2-hydroxyethyl)amino-5,6-dideoxy-β-L-ido-heptofuranose

(2S,3R,4R,5S)-1,2-Bis-(2-hydroxy-ethyl)-piperidine-3,4,5-triol

3-hydroxy-1,2-O-isopropylidene-5-(N-β-acetoxyethyl,N-benzyloxycarbonyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose

1,2-O-isopropylidene-3-O-benzyl-5-(N-β-acetoxyethyl-N-benzyl)amino-7-O-acetyl-5,6-dideoxy-β-L-ido-heptofuranose