(3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

Base Information

• Chemical Name: (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine
• CAS No.: 179536-80-2
• Molecular Formula: C₁₉H₂₉NO₅S
• Molecular Weight: 383.509
• Mol file: 179536-80-2.mol

Synonyms:(3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

Chemical Property of (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

There total 9 articles about (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine 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: 95.0%

(3R,4S,6S,9aS)-(-)-{[(2,2-dimethyl)diphenylsiloxy]methyl}-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)octahydro-2H-quinolizine (179536-79-9) → (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine (179536-80-2)

Guidance literature:

With pyridine; hydrogen fluoride; In tetrahydrofuran;

DOI:10.1021/jo9608174

Reference yield:

diethyl phenylsulfonylmethylphosphonate (56069-39-7) → (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine (179536-80-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) Swern reagent, 2) NaH / 2) THF

2: 94 percent / NH₄OAc / 10percent Cd-Pb / tetrahydrofuran / 48 h / Ambient temperature

3: 1) 10 percent HCl, 2) imidazole / 1) EtOH, reflux, 2) DMF, 80 deg C

4: 93 percent / Huenig base / CHCl₃ / Heating

5: 95 percent / HF, pyridine / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; swern reagent; hydrogen fluoride; ammonium acetate; sodium hydride; N-ethyl-N,N-diisopropylamine; 10% Cd/Pd; In tetrahydrofuran; chloroform;

DOI:10.1021/jo9608174

Reference yield:

ethyl (4aS,6R,8aR)-(+)-hexahydro-2,2-dimethyl-5-(phenylmethyl)-4H-1,3-dioxino-[5,4-b]pyridine-6-but-(2E)-enoate (179536-74-4) → (3R,4S,6S,9aS)-(-)-4-(hydroxymethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine (179536-80-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) H₂, 2) LiAlH₄, 3) K₂CO₃ / 1) Pd(OH)2 / 1) EtOH, 2) THF, reflux, 3) CHCl₃, H₂O

2: 1) Swern reagent, 2) NaH / 2) THF

3: 94 percent / NH₄OAc / 10percent Cd-Pb / tetrahydrofuran / 48 h / Ambient temperature

4: 1) 10 percent HCl, 2) imidazole / 1) EtOH, reflux, 2) DMF, 80 deg C

5: 93 percent / Huenig base / CHCl₃ / Heating

6: 95 percent / HF, pyridine / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; swern reagent; hydrogen fluoride; ammonium acetate; hydrogen; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; 10% Cd/Pd; In tetrahydrofuran; chloroform;

DOI:10.1021/jo9608174

upstream raw materials:

(3R,4S,6S,9aS)-(-)-{[(2,2-dimethyl)diphenylsiloxy]methyl}-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)octahydro-2H-quinolizine

(4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene

(3R,4S,6S,9aS)-(-)-4-{[(2,2-dimethylethyl)diphenylsiloxy]methyl}-3-hydroxy-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

(3R,4S,6S,9aS)-6-Benzenesulfonylmethyl-4-hydroxymethyl-octahydro-quinolizin-3-ol

Downstream raw materials:

(3R,4S,6S,9aS)-6-((1E,3E)-deca-1,3-dienyl)-4-methyl-octahydro-quinolizin-3-ol

(-)-clavepictine A

(3R,4S,6S,9aS)-(-)-3-(methoxymethoxy)-4-methyl-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

(3R,4S,6S,9aS)-(+)-4-(iodomethyl)-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine