3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

Base Information

Chemical Name:3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one
CAS No.:860465-56-1
Molecular Formula:C₃₁H₅₁BrO₆Si
Molecular Weight:627.732
Hs Code.:

3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

Synonyms:3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

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Chemical Property of 3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

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Technology Process of 3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

There total 11 articles about 3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one 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:

: 106-24-1
Geraniol

: 860465-56-1
3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: (-)-DET; 4 Angstroem molecular sieves; Ti(O-i-Pr)4 / t-BuOOH / toluene; CH₂Cl₂ / 0 h / -20 °C

2: NBS; H₂O / tetrahydrofuran / 2 h / 0 °C

3: CSA / diethyl ether / 1 h / 20 °C

4: aq. NaIO₄ / tetrahydrofuran / 3 h / 20 °C

5: 86 percent / tetrahydrofuran / 1 h / 0 °C

6: 1.1 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7: 0.54 g / Cp₂TiCl₂; Mn; 4 Angstroem molecular sieves / tetrahydrofuran / 0.75 h / 20 °C

With titanium(IV) isopropylate; bis(cyclopentadienyl)titanium dichloride; manganese; sodium periodate; N-Bromosuccinimide; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; water; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; tert.-butylhydroperoxide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1: Sharpless asymmetric epoxidation / 6: Swern oxidation;
DOI:10.1021/jo050465d

Reference yield:

: 860465-40-3
1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propenone

: ((1S,3R,5R,6S)-3-Benzyloxymethyl-1-methyl-2,7-dioxa-bicyclo[4.1.0]hept-5-yloxy)-tert-butyl-dimethyl-silane

: 860465-56-1
3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

Guidance literature:: With bis(cyclopentadienyl)titanium dichloride; manganese; 4 A molecular sieve; In tetrahydrofuran; at 20 ℃; for 0.75h;
DOI:10.1021/jo050465d

Reference yield:

: 860465-60-7
1-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

: 860465-56-1
3-[6-benzyloxymethyl-4-(tert-butyldimethylsilanyloxy)-3-hydroxy-2-methyl-(2S,3S,4R,6R)-tetrahydropyran-2-yl]-1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1.1 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 0.54 g / Cp₂TiCl₂; Mn; 4 Angstroem molecular sieves / tetrahydrofuran / 0.75 h / 20 °C

With bis(cyclopentadienyl)titanium dichloride; manganese; oxalyl dichloride; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo050465d