2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol

Base Information

• Chemical Name: 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol
• CAS No.: 860465-57-2
• Molecular Formula: C₂₅H₃₇BrO₅
• Molecular Weight: 497.47
• Mol file: 860465-57-2.mol

Synonyms:2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol

Chemical Property of 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol

There total 13 articles about 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-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: 51.0%

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 (860465-56-1) → 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol (860465-57-2)

Guidance literature:

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/jo050465d

Reference yield:

Geraniol (106-24-1) → 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol (860465-57-2)

Guidance literature:

Multi-step reaction with 8 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

8: 51 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.25 h / 0 °C

With titanium(IV) isopropylate; triethylsilane; bis(cyclopentadienyl)titanium dichloride; manganese; sodium periodate; N-Bromosuccinimide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 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:

1-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-en-1-ol (860465-60-7) → 2-benzyloxymethyl-6-[5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl]-8a-methyl-(2R,4R,4aS,8aS)-octahydropyrano[3,2-b]pyran-4-ol (860465-57-2)

Guidance literature:

Multi-step reaction with 3 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

3: 51 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.25 h / 0 °C

With triethylsilane; bis(cyclopentadienyl)titanium dichloride; manganese; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

DOI:10.1021/jo050465d

upstream raw materials:

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

1-(5-bromo-2,6,6-trimethyl-(2S,5R)-tetrahydropyran-2-yl)propenone

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

3-bromo-5-(3-hydroxymethyl-2-methyloxiranyl)-2-methyl-(2R,3R)-pentan-2-ol