(4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol

Base Information

• Chemical Name: (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol
• CAS No.: 1054667-48-9
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• Mol file: 1054667-48-9.mol

Synonyms:(4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol

Chemical Property of (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol

There total 12 articles about (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol 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%

(3R,5R,6S,6aR,10aS)-5,6-Dihydroxy-8,8-dimethyl-3-phenyl-tetrahydro-1,7,9-trioxa-3a-aza-cyclopenta[d]naphthalen-4-one (737799-98-3) → (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol (1054667-48-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1016/j.tetlet.2004.05.089

Reference yield:

6-benzyloxymethyl-3,4-dihydro-2H-pyran (89429-82-3) → (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol (1054667-48-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-CPBA / 2 h / 0 °C

1.2: 77 percent / DIPEA / 20 h / 20 °C

2.1: 40 percent / Jones reagent / acetone / 5 h / 20 °C

3.1: 72 percent / toluene / 12 h / Heating

4.1: NaI; CeCl₃*7H₂O / acetonitrile / 6 h / Heating

5.1: Jones reagent / acetone / 1 h / 20 °C

6.1: 87 percent / CeCl₃*7H₂O; NaBH₄ / ethanol; tetrahydrofuran / 1.5 h / 20 °C

7.1: 81 percent / BF₃*Et₂O; SMe₂ / 12 h / 20 °C

8.1: 75 percent / p-TsOH / CH₂Cl₂ / 3 h / 20 °C

9.1: KH; PhSO₂Me / tetrahydrofuran / 20 °C

9.2: 76 percent / toluene / 15 h / Heating

10.1: 82 percent / OsOO₄; NMO; t-BuOH / acetonitrile / 72 h

11.1: 90 percent / LiAlH₄ / tetrahydrofuran / 15 h / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; N-methyl-2-indolinone; jones reagent; cerium(III) chloride; dimethylsulfide; methylphenylsulfonate; boron trifluoride diethyl etherate; potassium hydride; toluene-4-sulfonic acid; sodium iodide; tert-butyl alcohol; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene; acetonitrile; 2.1: Jones oxidation / 5.1: Jones oxidation / 6.1: Luche reduction;

DOI:10.1016/j.tetlet.2004.05.089

Reference yield:

(3R,8R,8aS)-8-Hydroxy-8a-hydroxymethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one (737800-02-1) → (4aR,7S,8S,8aS)-5-((R)-2-Hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-7,8-diol (1054667-48-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / p-TsOH / CH₂Cl₂ / 3 h / 20 °C

2.1: KH; PhSO₂Me / tetrahydrofuran / 20 °C

2.2: 76 percent / toluene / 15 h / Heating

3.1: 82 percent / OsOO₄; NMO; t-BuOH / acetonitrile / 72 h

4.1: 90 percent / LiAlH₄ / tetrahydrofuran / 15 h / 20 °C

With lithium aluminium tetrahydride; N-methyl-2-indolinone; methylphenylsulfonate; potassium hydride; toluene-4-sulfonic acid; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2004.05.089

upstream raw materials:

(3R,5R,6S,6aR,10aS)-5,6-Dihydroxy-8,8-dimethyl-3-phenyl-tetrahydro-1,7,9-trioxa-3a-aza-cyclopenta[d]naphthalen-4-one

6-benzyloxymethyl-3,4-dihydro-2H-pyran

(3R,8R,8aS)-8-Hydroxy-8a-hydroxymethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

8,8-dimethyl-3-phenyl-2,3-dihydro-6aH-1,7,9-trioxa-3a-aza-cyclopenta[d]naphthalen-4-one