(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Base Information

Chemical Name:(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate
CAS No.:910043-27-5
Molecular Formula:C₃₂H₄₃BrO₇Si
Molecular Weight:647.679
Hs Code.:

(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Synonyms:(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Suppliers and Price of (+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

There total 11 articles about (+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate 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: 84.0%

: 910043-04-8
(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-hydroxy-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

: 107-30-2
chloromethyl methyl ether

: 910043-27-5
(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 - 40 ℃; for 26h;
DOI:10.1021/ja0581346

Reference yield:

: 910042-98-7
tert-butyl (2E,4E)-octa-2,4,6-trienoate

: 910043-27-5
(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 70 g / K₂CO₃; CH₃SO₂NH₂; quinuclidine / K₂Os₂O₂(OH)4; K₃Fe(CN)6 / 2-methyl-propan-2-ol; H₂O / 6 h / 20 °C

2.1: 43.8 g / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

3.1: 26.8 g / NaBH₄; MeOH / tetrahydrofuran / 3 h / cooling

4.1: AgOTf; Na₂CO₃; 2,6-lutidine / CH₂Cl₂ / 0.33 h / cooling

4.2: CH₂Cl₂ / 16.5 h / -78 - 20 °C

4.3: 10.0 g / toluene / 14 h / 20 °C

5.1: 53 percent / NaHCO₃ / xylene / 114 h / Heating

6.1: 7.7 g / mCPBA; NaH₂PO₄*H₂O / CH₂Cl₂ / 21 h / 0 - 20 °C

7.1: 84 percent / DBU / tetrahydrofuran / 20 h / 20 °C

8.1: 100 percent / TFA / 0.5 h / 20 °C

9.1: ethyl chloroformate; triethylamine / CH₂Cl₂ / 0.5 h / cooling

9.2: 100 percent / NaBH₄; MeOH / tetrahydrofuran / 1.17 h / -40 - 0 °C

10.1: 4.0 g / DMAP; triethylamine / CH₂Cl₂ / 17 h / 0 - 20 °C

11.1: 84 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 26 h / 20 - 40 °C

With Quinuclidine; 2,6-dimethylpyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; methanesulfonamide; silver trifluoromethanesulfonate; chloroformic acid ethyl ester; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; potassium osmate; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; xylene; tert-butyl alcohol; 5.1: intramolecular Diels-Alder reactiom;
DOI:10.1021/ja0581346

Reference yield:

: 910043-00-4
tert-butyl (E,E)-6-formylpenta-2,4-dienoate

: 910043-27-5
(+)-isopropyl 2α-bromomethyl-7-(tert-butyldiphenylsilyloxymethyl)-5β-(methoxymethoxy)-4aβ,5,8,8a-tetrahydro-4H-1,3-benzodioxin-8aβ-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 26.8 g / NaBH₄; MeOH / tetrahydrofuran / 3 h / cooling

2.1: AgOTf; Na₂CO₃; 2,6-lutidine / CH₂Cl₂ / 0.33 h / cooling

2.2: CH₂Cl₂ / 16.5 h / -78 - 20 °C

2.3: 10.0 g / toluene / 14 h / 20 °C

3.1: 53 percent / NaHCO₃ / xylene / 114 h / Heating

4.1: 7.7 g / mCPBA; NaH₂PO₄*H₂O / CH₂Cl₂ / 21 h / 0 - 20 °C

5.1: 84 percent / DBU / tetrahydrofuran / 20 h / 20 °C

6.1: 100 percent / TFA / 0.5 h / 20 °C

7.1: ethyl chloroformate; triethylamine / CH₂Cl₂ / 0.5 h / cooling

7.2: 100 percent / NaBH₄; MeOH / tetrahydrofuran / 1.17 h / -40 - 0 °C

8.1: 4.0 g / DMAP; triethylamine / CH₂Cl₂ / 17 h / 0 - 20 °C

9.1: 84 percent / iPr₂NEt; DMAP / CH₂Cl₂ / 26 h / 20 - 40 °C

With 2,6-dimethylpyridine; methanol; dmap; sodium tetrahydroborate; sodium dihydrogenphosphate; silver trifluoromethanesulfonate; chloroformic acid ethyl ester; sodium hydrogencarbonate; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; xylene; 3.1: intramolecular Diels-Alder reactiom;
DOI:10.1021/ja0581346