Acetonitrile, ((2S,3R,4S,6R)-6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (2Z)-

Base Information

• Chemical Name: Acetonitrile, ((2S,3R,4S,6R)-6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (2Z)-
• CAS No.: 51771-52-9
• Molecular Formula: C16H25 N O9
• Molecular Weight: 375.37
• UNII: O51H15R39K
• DSSTox Substance ID: DTXSID901027519
• Wikipedia: Simmondsin
• Wikidata: Q2287286
• Mol file: 51771-52-9.mol

Synonyms:2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl-beta-glucoside;simmondsin

Chemical Property of Acetonitrile, ((2S,3R,4S,6R)-6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (2Z)-

Chemical Property:

• Vapor Pressure: 6.16E-19mmHg at 25°C
• Melting Point: 95～100℃
• Boiling Point: 637.5°Cat760mmHg
• Flash Point: 339.4°C
• PSA: 161.86000
• Density: 1.45g/cm³
• LogP: -2.58392
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 375.15293138
• Heavy Atom Count: 26
• Complexity: 547

Purity/Quality:

99% ^*data from raw suppliers

Simmondsin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1CC(C(=CC#N)C(C1OC)O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: CO[C@H]1C[C@H](/C(=C\C#N)/[C@@H]([C@H]1OC)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Simmondsin derived from the Jojoba plant (Simmondsia chinensis). Purified simmondsin from jojoba meal has been shown to decrease food intake in adult rats.

Technology Process of Acetonitrile, ((2S,3R,4S,6R)-6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (2Z)-

There total 18 articles about Acetonitrile, ((2S,3R,4S,6R)-6-(beta-D-glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene)-, (2Z)- 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%

(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane (135131-70-3) → (7Z)-(1R,3S,4R,5S)-2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucopyranoside (51771-52-9)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃;

DOI:10.1039/c39910000588

Reference yield: 100.0%

simmondsin penta-O-acetate (51385-17-2) → (7Z)-(1R,3S,4R,5S)-2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucopyranoside (51771-52-9)

Guidance literature:

With methanol; sodium methylate; at 0 ℃; for 2h;

Reference yield:

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6) → (7Z)-(1R,3S,4R,5S)-2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucopyranoside (51771-52-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 1) NaH / 1) DMF, 0 deg C, 40 min, 2) r.t., 30 min

2: 81 percent / pTsOH*H₂O / methanol / 7 h / 0 °C

3: 1) pyridine, 2) pyridine / 1) 0 deg C, 27 h, 2) r.t., 6 h

4: 84 percent / NaOMe / methanol / 3 h / Ambient temperature

5: 91 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

6: 1) NaH / 1) DMF, 0 deg C, 45 min, 2) r.t., 12 h

7: 92 percent / pTsOH / methanol / 4 h / Ambient temperature

8: 87 percent / pyridine / 13 h / 70 °C

9: 98 percent / pTsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 89 percent / NaOMe / methanol / 9 h / 50 °C

11: 87 percent / PCC, molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

12: 43 percent / KOtBu / toluene / 6 h / Ambient temperature

13: 97 percent / pyridinium toluene-p-sulfonate / ethanol / 4 h / 50 °C

14: 100 percent / pyridine / 2 h / Ambient temperature

15: 72 percent / DDQ, H₂O / CH₂Cl₂ / 18 h / Ambient temperature

16: 27 percent / molecular sieves, BF₃*OEt₂ / 1,2-dichloro-ethane / 0.33 h / 0 °C

17: 100 percent / NaOMe, MeOH / 2 h / 0 °C

With pyridine; methanol; lithium aluminium tetrahydride; molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; water; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

upstream raw materials:

(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane

simmondsin penta-O-acetate

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

1D-(1,2,5/3,4)-3,4-O-isopropylidene-1,2-di-O-methylcyclohexanepentaol

Downstream raw materials:

2-(2-hydroxy-3-methoxyphenyl)acetonitrile

Refernces

• 1、 Chida, Noritaka,Yamada, Ken,Ogawa, Seiichiro. "Total Synthesis of Simmondsin". . p. 588 - 590. Retrieved 2007/10/02.