beta-L-lyxo-Heptopyranoside, methyl 2,3,4,6,7-pentadeoxy-2,6-bis(((phenylmethoxy)carbonyl)amino)-

Base Information

• Chemical Name: beta-L-lyxo-Heptopyranoside, methyl 2,3,4,6,7-pentadeoxy-2,6-bis(((phenylmethoxy)carbonyl)amino)-
• CAS No.: 99239-15-3
• Molecular Formula: C₂₄H₃₀N₂O₆
• Molecular Weight: 442.512
• DSSTox Substance ID: DTXSID30912824
• Wikidata: Q82883236
• Mol file: 99239-15-3.mol

Synonyms:6-epipurpurosamine B;methyl 2.6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-beta-lyxo-heptopyranoside

Chemical Property of beta-L-lyxo-Heptopyranoside, methyl 2,3,4,6,7-pentadeoxy-2,6-bis(((phenylmethoxy)carbonyl)amino)-

Chemical Property:

• Vapor Pressure: 2.24E-15mmHg at 25°C
• Boiling Point: 621.6°C at 760 mmHg
• Flash Point: 329.8°C
• PSA: 95.12000
• Density: 1.22g/cm³
• LogP: 4.52960
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 442.21038668
• Heavy Atom Count: 32
• Complexity: 577

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC(C(O1)OC)NC(=O)OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C[C@@H]([C@@H]1CC[C@H]([C@H](O1)OC)NC(=O)OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

Technology Process of beta-L-lyxo-Heptopyranoside, methyl 2,3,4,6,7-pentadeoxy-2,6-bis(((phenylmethoxy)carbonyl)amino)-

There total 18 articles about beta-L-lyxo-Heptopyranoside, methyl 2,3,4,6,7-pentadeoxy-2,6-bis(((phenylmethoxy)carbonyl)amino)- 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:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → methyl 2,6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside (99239-15-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) HCl / 1.) 6 h, reflux, 2.) pyridine, 5.5 h, room temp., 2 h, 100 deg C

2: 81 percent / pyridine / Ambient temperature

3: 67 percent / Zn, NaI / dimethylformamide / 5.5 h / 95 °C

4: 3.74 g / H₂ / 10percent Pd-C / ethyl acetate; acetic acid / 6 h / 760 Torr / Ambient temperature

5: 78 percent / Et₃N / CH₂Cl₂ / 1.) 2 h, room temp., 2.) overnight, room temp., 3.) 5 h, reflux

6: 81 percent / aq. acetic acid / 0.5 h / 100 °C

7: 78 percent / Me₂SO, DCC, pyridine, CF₃COOH / 1.) room temp., overnight, 2.) 40 deg C, 30 min

8: 1.) THF, -20 - -15 deg C, 20 min, 2.) pyridine, room temp., 1 d

9: 53 percent / dimethylformamide / 18 h / Heating

10: H₂NNH₂*H₂O / ethanol / 2 h / Heating

11: M NaOH / acetone; H₂O / 0.5 h / Ambient temperature

12: KOH / methanol / 2 h / Ambient temperature

13: 99 percent / pyridine / Ambient temperature

14: 94 percent / NaN₃ / dimethylformamide / 1.5 h / 100 °C

15: H₂ / Pd black / ethyl acetate; acetic acid / 5 h / 2660 Torr / Ambient temperature

16: M NaOH / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium azide; hydrogen; hydrazine hydrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; zinc; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(86)85023-6

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl 2,6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside (99239-15-3)

Guidance literature:

Multi-step reaction with 6 steps

1: M NaOH / acetone; H₂O / 0.5 h / Ambient temperature

2: KOH / methanol / 2 h / Ambient temperature

3: 99 percent / pyridine / Ambient temperature

4: 94 percent / NaN₃ / dimethylformamide / 1.5 h / 100 °C

5: H₂ / Pd black / ethyl acetate; acetic acid / 5 h / 2660 Torr / Ambient temperature

6: M NaOH / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; sodium azide; hydrogen; palladium; In tetrahydrofuran; pyridine; methanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0008-6215(86)85023-6

Reference yield:

methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-α-D-ribo-heptopyranoside (99239-12-0) → methyl 2,6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside (99239-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / pyridine / Ambient temperature

2: 94 percent / NaN₃ / dimethylformamide / 1.5 h / 100 °C

3: H₂ / Pd black / ethyl acetate; acetic acid / 5 h / 2660 Torr / Ambient temperature

4: M NaOH / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

With sodium hydroxide; sodium azide; hydrogen; palladium; In tetrahydrofuran; pyridine; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)85023-6

upstream raw materials:

benzyl chloroformate

6-epipurpurosamine B

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

methyl 2,6-bis(acetamido)-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

Refernces