Tenuifoliside B

Base Information

• Chemical Name: Tenuifoliside B
• CAS No.: 139726-36-6
• Molecular Formula: C₃₀H₃₆O₁₇
• Molecular Weight: 668.606
• UNII: F38VD25Q1W
• Nikkaji Number: J2.067.107F
• Wikidata: Q27277574
• Mol file: 139726-36-6.mol

Synonyms:Tenuifoliside B;139726-36-6;(-)-Tenuifoliside B;UNII-F38VD25Q1W;F38VD25Q1W;[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl 4-hydroxybenzoate;alpha-D-Glucopyranoside, 3-O-((2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propen-1-yl)-beta-D-fructofuranosyl, 6-(4-hydroxybenzoate);alpha-D-Glucopyranoside, 3-O-((2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)-beta-D-fructofuranosyl, 6-(4-hydroxybenzoate);alpha-D-Glucopyranoside, 3-O-(3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)-beta-D-fructofuranosyl, 6-(4-hydroxybenzoate), (E)-;HY-N4268;AKOS037515198;MS-31045;CS-0032592;D84995;Q27277574;.ALPHA.-D-GLUCOPYRANOSIDE, 3-O-((2E)-3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-1-OXO-2-PROPEN-1-YL)-.BETA.-D-FRUCTOFURANOSYL, 6-(4-HYDROXYBENZOATE);.ALPHA.-D-GLUCOPYRANOSIDE, 3-O-((2E)-3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)-.BETA.-D-FRUCTOFURANOSYL, 6-(4-HYDROXYBENZOATE);.ALPHA.-D-GLUCOPYRANOSIDE, 3-O-(3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)-.BETA.-D-FRUCTOFURANOSYL, 6-(4-HYDROXYBENZOATE), (E)-

Chemical Property of Tenuifoliside B

Chemical Property:

• Boiling Point: 926.1±65.0 °C(Predicted)
• PKA: 8.13±0.15(Predicted)
• PSA: 260.59000
• Density: 1.61±0.1 g/cm3(Predicted)
• LogP: -1.83820
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 14
• Exact Mass: 668.19524968
• Heavy Atom Count: 47
• Complexity: 1040

Purity/Quality:

≥98% ^*data from raw suppliers

Tenuifoliside B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(C(OC2(CO)OC3C(C(C(C(O3)COC(=O)C4=CC=C(C=C4)O)O)O)O)CO)O
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=CC=C(C=C4)O)O)O)O)CO)O

Technology Process of Tenuifoliside B

There total 7 articles about Tenuifoliside B 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: 90.0%

C34H40O19 → Tenuifoliside B (139726-36-6,145316-84-3)

Guidance literature:

With ammonium acetate; water; In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2014.04.050

Reference yield:

(E)-4-acetoxy-3,5-dimethoxycinnamic acid (90985-68-5,113158-15-9) → Tenuifoliside B (139726-36-6,145316-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis(trichloromethyl) carbonate; triethylamine / ethyl acetate / 0.42 h / 0 - 20 °C

2.1: cobalt(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

2.2: 1 h / 20 °C

3.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide / 0.5 h / 0 - 75 °C

4.1: ammonium acetate; water / methanol / 24 h / 20 °C

With bis(trichloromethyl) carbonate; di-isopropyl azodicarboxylate; ammonium acetate; water; triethylamine; triphenylphosphine; cobalt(II) chloride; In methanol; ethyl acetate; N,N-dimethyl-formamide; 3.1: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2014.04.050

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → Tenuifoliside B (139726-36-6,145316-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 2 h / Reflux

2: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide / 0.5 h / 0 - 75 °C

3: ammonium acetate; water / methanol / 24 h / 20 °C

With pyridine; di-isopropyl azodicarboxylate; ammonium acetate; water; triphenylphosphine; In methanol; N,N-dimethyl-formamide; 2: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2014.04.050

upstream raw materials:

syringic aldehyde

(E)-4-acetoxy-3,5-dimethoxycinnamic acid

4-hydroxy-benzoic acid

4-acetyloxy-benzoic acid

Downstream raw materials:

methyl (E)-sinapate

sibiricose A₃