benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate

Base Information

• Chemical Name: benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate
• CAS No.: 1323207-91-5
• Molecular Formula: C₄₆H₅₉NO₂₆
• Molecular Weight: 1041.97

Synonyms:

Chemical Property of benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate

There total 6 articles about benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate 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:

1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (908142-25-6) → benzyl (3S,4S,5R)-3,4-diacetoxy-5-(tri-O-acetyl-β-D-xylopyranosyloxy)piperidine-1-carboxylate (1323207-86-8) + benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate (1323207-91-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium periodate / methanol; water

2.1: hydrogenchloride / tetrahydrofuran / 16 h / 20 °C

3.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen; benzylamine / methanol / 48 h / 2280.15 Torr

4.1: potassium carbonate / methanol; water / 16 h

5.1: Bhxglycosynthase E₃₃₄G mutant / 24 h / 20 °C / pH 7 / aq. phosphate buffer; Enzymatic reaction

5.2: 16 h / 20 °C

With hydrogenchloride; sodium periodate; palladium 10% on activated carbon; Bhxglycosynthase E₃₃₄G mutant; hydrogen; potassium carbonate; benzylamine; In tetrahydrofuran; methanol; water;

DOI:10.1002/cbic.201100229

Reference yield:

3-O-benzylxylopentodialdo-1,4-furanose → benzyl (3S,4S,5R)-3,4-diacetoxy-5-(tri-O-acetyl-β-D-xylopyranosyloxy)piperidine-1-carboxylate (1323207-86-8) + benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate (1323207-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen; benzylamine / methanol / 48 h / 2280.15 Torr

2.1: potassium carbonate / methanol; water / 16 h

3.1: Bhxglycosynthase E₃₃₄G mutant / 24 h / 20 °C / pH 7 / aq. phosphate buffer; Enzymatic reaction

3.2: 16 h / 20 °C

With hydrogenchloride; palladium 10% on activated carbon; Bhxglycosynthase E₃₃₄G mutant; hydrogen; potassium carbonate; benzylamine; In methanol; water;

DOI:10.1002/cbic.201100229

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (3S,4S,5R)-3,4-diacetoxy-5-(tri-O-acetyl-β-D-xylopyranosyloxy)piperidine-1-carboxylate (1323207-86-8) + benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate (1323207-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / methanol; water / 16 h

2.1: Bhxglycosynthase E₃₃₄G mutant / 24 h / 20 °C / pH 7 / aq. phosphate buffer; Enzymatic reaction

2.2: 16 h / 20 °C

With Bhxglycosynthase E₃₃₄G mutant; potassium carbonate; In methanol; water;

DOI:10.1002/cbic.201100229

upstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1,5-Dideoxy-1,5-iminoxylitol

benzyl chloroformate

1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

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