Phylanthoside

Base Information

• Chemical Name: Phylanthoside
• CAS No.: 63166-73-4
• Molecular Formula: C40H52O17
• Molecular Weight: 804.843
• NSC Number: 328426
• NCI Thesaurus Code: C29324
• ChEMBL ID: CHEMBL1722641
• Mol file: 63166-73-4.mol

Synonyms:phyllanthoside

Chemical Property of Phylanthoside

Chemical Property:

• Boiling Point: 872.8oC at 760 mmHg
• Flash Point: 260.4oC
• PSA: 224.57000
• Density: 1.41g/cm3
• LogP: 1.31250
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 13
• Exact Mass: 804.32045019
• Heavy Atom Count: 57
• Complexity: 1520

Purity/Quality:

99% ^*data from raw suppliers

Phyllanthoside - Phyllanthus acuminatus ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1COC2(CC1OC(=O)C=CC3=CC=CC=C3)C4(CO4)C5CCC(CC5O2)C(=O)OC6C(C(C(C(O6)C)O)OC(=O)C)OC7C(C(C(C(O7)C)O)OC(=O)C)O
• Isomeric SMILES: CC1COC2(CC1OC(=O)/C=C/C3=CC=CC=C3)C4(CO4)C5CCC(CC5O2)C(=O)OC6C(C(C(C(O6)C)O)OC(=O)C)OC7C(C(C(C(O7)C)O)OC(=O)C)O

Technology Process of Phylanthoside

There total 54 articles about Phylanthoside 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: 100.0%

C58H94O17Si3 (106711-70-0) → Phyllanthoside (63166-73-4)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; for 21h; Ambient temperature;

Reference yield:

3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose (18439-45-7,70632-45-0,87938-30-5,18439-44-6) → Phyllanthoside (63166-73-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 94 percent / 2 N H₂SO₄ / tetrahydrofuran / 48 h / 60 °C

2: 65 percent / camphorsulfonic acid (CSA) / tetrahydrofuran / 1.) rt, 20 h, 2.) 60 deg C, 6 h

3: 99 percent / DMAP, pyridine / CH₂Cl₂ / 0.33 h

4: camphorsulfonic acid (CSA) / benzene / 27 h / Heating

5: 75 percent / Hg(CN)2, 4A molecular sieves / benzene / 1 h / Ambient temperature

6: 73 percent / 10percent Pd/C / methanol / 4 h / Heating

7: K₂CO₃ / methanol; tetrahydrofuran / 23 h / Ambient temperature

8: DMAP, Et₃N / dimethylformamide / 12 h / Ambient temperature

9: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to rt

10: 88 percent / H₂ / 10percent Pd/C / ethyl acetate / Ambient temperature

11: 96 percent / 4-pyrrolidinopyridine, Et₃N / 4.5 h / Ambient temperature

12: 100 percent / Et₃N / methanol / 23 h / Ambient temperature

13: Ph₃P (TPP), diisopropyl azodicarboxylate (DIAD) / tetrahydrofuran / 27 h / Ambient temperature

14: 86 percent / NaBH₄ / methanol / 0.08 h / -20 °C

15: 93 percent / pyridine, Et₃N, 4-pyrrolidinopyridine / 24 h / Ambient temperature

16: 100 percent / H₂O, AcOH / tetrahydrofuran / 21 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; 4 A molecular sieve; sulfuric acid; camphor-10-sulfonic acid; water; hydrogen; mercury(II) cyanide; potassium carbonate; 4-pyrrolidin-1-ylpyridine; ozone; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

Reference yield:

3-O-Benzyl-6-deoxy-D-glucose (106711-50-6,134311-77-6) → Phyllanthoside (63166-73-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 65 percent / camphorsulfonic acid (CSA) / tetrahydrofuran / 1.) rt, 20 h, 2.) 60 deg C, 6 h

2: 99 percent / DMAP, pyridine / CH₂Cl₂ / 0.33 h

3: camphorsulfonic acid (CSA) / benzene / 27 h / Heating

4: 75 percent / Hg(CN)2, 4A molecular sieves / benzene / 1 h / Ambient temperature

5: 73 percent / 10percent Pd/C / methanol / 4 h / Heating

6: K₂CO₃ / methanol; tetrahydrofuran / 23 h / Ambient temperature

7: DMAP, Et₃N / dimethylformamide / 12 h / Ambient temperature

8: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to rt

9: 88 percent / H₂ / 10percent Pd/C / ethyl acetate / Ambient temperature

10: 96 percent / 4-pyrrolidinopyridine, Et₃N / 4.5 h / Ambient temperature

11: 100 percent / Et₃N / methanol / 23 h / Ambient temperature

12: Ph₃P (TPP), diisopropyl azodicarboxylate (DIAD) / tetrahydrofuran / 27 h / Ambient temperature

13: 86 percent / NaBH₄ / methanol / 0.08 h / -20 °C

14: 93 percent / pyridine, Et₃N, 4-pyrrolidinopyridine / 24 h / Ambient temperature

15: 100 percent / H₂O, AcOH / tetrahydrofuran / 21 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; 4 A molecular sieve; camphor-10-sulfonic acid; water; hydrogen; mercury(II) cyanide; potassium carbonate; 4-pyrrolidin-1-ylpyridine; ozone; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

upstream raw materials:

C₅₈H₉₄O₁₇Si₃

3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose

3-O-Benzyl-6-deoxy-D-glucose

C₁₈H₂₄O₅

Downstream raw materials:

phyllanthocin

phyllanthose

C₄₆H₅₈O₂₀

(+)-phyllanthostatin 2

Refernces