2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide

Base Information

• Chemical Name: 2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide
• CAS No.: 186664-06-2
• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.426
• Mol file: 186664-06-2.mol

Synonyms:2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide

Chemical Property of 2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide

There total 1 articles about 2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide 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: 91.0%

methanol (67-56-1) + 2-[(1S,2S,5S,7S)-7-(4-Methoxy-phenoxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-yl]-N,N-dimethyl-acetamide → 2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide (186664-06-2)

Guidance literature:

With toluene-4-sulfonic acid; at 0 ℃; for 7.5h;

DOI:10.1016/S0040-4039(97)82953-X

Reference yield: 90.0%

2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide (186664-06-2) → (3aR,4S,6S,7S,7aR)-4-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-7-iodo-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one (186664-07-3)

Guidance literature:

With iodine; In tetrahydrofuran; water; for 5h; Heating;

DOI:10.1016/S0040-4039(97)82953-X

Reference yield:

2-{(2S,3S,6S)-2-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-6-methoxy-3,6-dihydro-2H-pyran-3-yl}-N,N-dimethyl-acetamide (186664-06-2) → thromboxane B2 (54397-85-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / I₂ / tetrahydrofuran; H₂O / 5 h / Heating

2: 88 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

3: 98 percent / H₃PO₂ aq., AIBN, Et₃N / dioxane / 1 h / Heating

4: 96 percent / CAN, pyridine / H₂O; acetonitrile / 0.5 h / 0 °C

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to 0 deg C

6: 85 percent / CrCl₂ / dimethylformamide; tetrahydrofuran / 8 h / Heating

7: 87 percent / nBu₄NF*3H₂O / tetrahydrofuran / 7 h / Ambient temperature

8: 99 percent / pyridine / 2.5 h / Ambient temperature

9: 1) PdCl₂(CH₃CN)2, 2) DIBAL, 3) t-BuOK / 1) THF, 2 h, RT, 2) THF, -78 deg C, 14 h, 3) THF, 1 h, RT

10: 93 percent / H₃PO₄, H₂O / tetrahydrofuran / 6 h / 40 °C

With pyridine; 1H-imidazole; chromium dichloride; dichloro bis(acetonitrile) palladium(II); oxalyl dichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); phosphoric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; iodine; hypophosphorous acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(97)82953-X

upstream raw materials:

methanol

Downstream raw materials:

(3aR,4S,6S,7S,7aR)-4-[(S)-1-Hydroxy-2-(4-methoxy-phenoxy)-ethyl]-7-iodo-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one

thromboxane B₂

(3aS,4S,6S,7aS)-4-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one

(R)-(tert-Butyl-diphenyl-silanyloxy)-((3aS,4S,6S,7aS)-6-methoxy-2-oxo-hexahydro-furo[3,2-c]pyran-4-yl)-acetaldehyde