(3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Base Information

• Chemical Name: (3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS No.: 256341-98-7
• Molecular Formula: C₁₄H₁₈O₄Se
• Molecular Weight: 329.255
• Mol file: 256341-98-7.mol

Synonyms:(3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Chemical Property of (3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

There total 1 articles about (3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 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:

2-Methoxypropene (116-11-0) + phenyl 1-seleno-β-D-xylopyranoside (374115-40-9) → (3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (256341-98-7)

Guidance literature:

With trifluoroacetic acid; In N,N-dimethyl-formamide; at 45 ℃; for 3h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield: 95.0%

p-methoxybenzyl chloride (824-94-2) + (3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (256341-98-7) → (3aR,4S,7R,7aS)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (256341-99-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; at 0 - 25 ℃; for 2h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

(3aR,4S,7R,7aS)-2,2-Dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (256341-98-7) → C61H74O17Si (256342-28-6)

Guidance literature:

Multi-step reaction with 22 steps

1.1: NaH / dimethylformamide / 0.08 h / 0 °C

1.2: 95 percent / nBu₄NI / dimethylformamide / 2 h / 0 - 25 °C

2.1: 96 percent / PPTS; MeOH / 1 h / 25 °C

3.1: 91 percent / 2,6-lutidine / tetrahydrofuran / 0.5 h / -78 °C

4.1: 100 percent / DAST / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 92 percent / SnCl₂ / diethyl ether / 3 h / 0 - 25 °C

6.1: 98 percent / K₂CO₃; MeOH / diethyl ether / 1 h / 25 °C

7.1: aq. NaIO₄; NaHCO₃ / methanol; CH₂Cl₂ / 2 h / 25 °C

8.1: 430 mg / iPr₂NH; vinyl acetate / toluene / 12 h / 140 °C

9.1: 95 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

10.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

11.1: 95 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 25 °C

12.1: 85 percent / Martin sulfurane; Et₃N / CHCl₃ / 2 h / 50 °C

13.1: 90 percent / K₂CO₃; MeOH / 6 h / 25 °C

14.1: NaH; 18-crown-6 / tetrahydrofuran / 0.25 h / 0 °C

14.2: 80 percent / tetrahydrofuran / 2 h / 0 °C

15.1: NMO; H₂O; OsO₄ / quinuclidine / acetone / 36 h / 25 °C

16.1: nBu₂SnO / methanol / 3 h / Heating

16.2: dioxane / 0.5 h / 15 °C

17.1: 85 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 25 °C

18.1: 68 mg / Li(tBuO)3AlH / diethyl ether / 1 h / -10 °C

19.1: 98 percent / NaOH; MeOH / 1 h / 25 °C

20.1: 90 percent / aq. NaOH; nBu₄NBr / 2 h / 65 °C

21.1: 85 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C / pH 7

22.1: NaH / tetrahydrofuran / 0.08 h / 0 °C

22.2: 96 percent / tetrahydrofuran / 2 h / 0 - 25 °C

With 2,6-dimethylpyridine; methanol; dmap; sodium hydroxide; sodium periodate; osmium(VIII) oxide; vinyl acetate; N-methyl-2-indolinone; Martins sulfurane; 18-crown-6 ether; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; diisopropylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; Quinuclidine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; 1.1: Metallation / 1.2: Etherification / 2.1: Ring cleavage / 3.1: Etherification / 4.1: Rearrangement / 5.1: Glycosidation / 6.1: Deacylation / 7.1: Oxidation / 8.1: Cyclization / 9.1: Silyl ether cleavage / 10.1: Esterification / 11.1: Silyl ether cleavage / 12.1: Dehydration / 13.1: Debenzoylation / 14.1: Metallation / 14.2: Etherification / 15.1: Oxidation / 16.1: Cyclization / 16.2: Ring cleavage / 17.1: Oxidation / 18.1: Reduction / 19.1: Debenzoylation / 20.1: Cyclization / 21.1: Oxidatio;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

upstream raw materials:

2-Methoxypropene

phenyl 1-seleno-β-D-xylopyranoside

Downstream raw materials:

(3aR,4S,7R,7aS)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

(2S,3R,4R,5R)-5-(4-Methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-3,4-diol

tert-Butyl-[(3S,4S,5R)-2-fluoro-5-(4-methoxy-benzyloxy)-3-phenylselanyl-tetrahydro-pyran-4-yloxy]-dimethyl-silane

(2S,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-phenylselanyl-tetrahydro-pyran-3-ol