simmondsin penta-O-acetate

Base Information

• Chemical Name: simmondsin penta-O-acetate
• CAS No.: 51385-17-2
• Molecular Formula: C₂₆H₃₅NO₁₄
• Molecular Weight: 585.562
• Mol file: 51385-17-2.mol

Synonyms:simmondsin penta-O-acetate

Chemical Property of simmondsin penta-O-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of simmondsin penta-O-acetate

There total 18 articles about simmondsin penta-O-acetate 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: 27.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane (135131-70-3) → simmondsin penta-O-acetate (51385-17-2)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 0 ℃; for 0.5h;

DOI:10.1039/c39910000588

Reference yield:

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6) → simmondsin penta-O-acetate (51385-17-2)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; 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;

Reference yield:

1D-(1,2,5/3,4)-3,4-O-isopropylidene-1,2-di-O-methylcyclohexanepentaol (135131-63-4) → simmondsin penta-O-acetate (51385-17-2)

Guidance literature:

Multi-step reaction with 11 steps

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

2: 92 percent / pTsOH / methanol / 4 h / Ambient temperature

3: 87 percent / pyridine / 13 h / 70 °C

4: 98 percent / pTsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 89 percent / NaOMe / methanol / 9 h / 50 °C

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

7: 43 percent / KOtBu / toluene / 6 h / Ambient temperature

8: 97 percent / pyridinium toluene-p-sulfonate / ethanol / 4 h / 50 °C

9: 100 percent / pyridine / 2 h / Ambient temperature

10: 72 percent / DDQ, H₂O / CH₂Cl₂ / 18 h / Ambient temperature

11: 27 percent / molecular sieves, BF₃*OEt₂ / 1,2-dichloro-ethane / 0.33 h / 0 °C

With pyridine; 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 methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

upstream raw materials:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

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

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:

(7Z)-(1R,3S,4R,5S)-2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucopyranoside

Refernces

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