7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol

Base Information

• Chemical Name: 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol
• CAS No.: 77878-41-2
• Molecular Formula: C₂₀H₃₁BrO₄
• Molecular Weight: 415.368
• Mol file: 77878-41-2.mol

Synonyms:7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol

Chemical Property of 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol

There total 13 articles about 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-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:

11-benzyloxy-1-bromo-6,10-dimethyl-5,6-epoxy-undecan-2-one (77878-39-8) → 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol (77878-41-2)

Guidance literature:

With hydrogenchloride; In acetone; 1) 0 deg C, 0.75 h, 2) RT, 18 h;

DOI:10.1021/jo00188a017

Reference yield:

5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone (15580-05-9) → 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol (77878-41-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 38 percent / tetrahydrofuran / 1.5 h / Ambient temperature

2: 1)BH₃*Me₂S, 2) 3N NaOH, 30percent H₂O₂ / 1) hexane, a) 0 deg C, b) 3h at RT; 2) ethanol, a) 25 - 35 deg C, b) reflux

3: NaH / benzene / 16 h / Heating

4: 70 percent / 10 percent HCl / acetone / 3 h / Ambient temperature

5: 82 percent / NaH / benzene / 2 h / 70 °C

6: 17.7 percent / LAH / diethyl ether / 4 h / 0 °C

7: 19.7 g / LiCl, CH₃SO₂Cl, collidine / dimethylformamide / 1) 0 deg C, 0.75 h, 2) RT, 2h

8: NaOEt / 1) 0 deg C, 1.5h, 2) RT, 2h

9: 12.4 g / 2 N NaOH/MeOH, H₂O / 3 h / Heating

10: 15.36 g / LDA, triethylamine / tetrahydrofuran / 4 h / -70 °C

11: NaHCO₃, NBS / tetrahydrofuran / 4 h / -70 °C

12: 85 percent MCPBA / CH₂Cl₂ / 3 h / 0 °C

13: 0.2 N HCl / acetone / 1) 0 deg C, 0.75 h, 2) RT, 18 h

With 2,3,5-trimethyl-pyridine; hydrogenchloride; methanol; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dimethylsulfide borane complex; water; dihydrogen peroxide; sodium ethanolate; sodium hydride; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00188a017

Reference yield:

2-Methyl-2-(4-methyl-4-pentenyl)-1,3-dioxolane (38237-34-2) → 7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)6-methyl-heptan-2-ol (77878-41-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 1)BH₃*Me₂S, 2) 3N NaOH, 30percent H₂O₂ / 1) hexane, a) 0 deg C, b) 3h at RT; 2) ethanol, a) 25 - 35 deg C, b) reflux

2: NaH / benzene / 16 h / Heating

3: 70 percent / 10 percent HCl / acetone / 3 h / Ambient temperature

4: 82 percent / NaH / benzene / 2 h / 70 °C

5: 17.7 percent / LAH / diethyl ether / 4 h / 0 °C

6: 19.7 g / LiCl, CH₃SO₂Cl, collidine / dimethylformamide / 1) 0 deg C, 0.75 h, 2) RT, 2h

7: NaOEt / 1) 0 deg C, 1.5h, 2) RT, 2h

8: 12.4 g / 2 N NaOH/MeOH, H₂O / 3 h / Heating

9: 15.36 g / LDA, triethylamine / tetrahydrofuran / 4 h / -70 °C

10: NaHCO₃, NBS / tetrahydrofuran / 4 h / -70 °C

11: 85 percent MCPBA / CH₂Cl₂ / 3 h / 0 °C

12: 0.2 N HCl / acetone / 1) 0 deg C, 0.75 h, 2) RT, 18 h

With 2,3,5-trimethyl-pyridine; hydrogenchloride; methanol; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dimethylsulfide borane complex; water; dihydrogen peroxide; sodium ethanolate; sodium hydride; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00188a017

upstream raw materials:

11-benzyloxy-1-bromo-6,10-dimethyl-5,6-epoxy-undecan-2-one

5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone

2-Methyl-2-(4-methyl-4-pentenyl)-1,3-dioxolane

2-(5-hydroxy-4-methylpentyl)-2-methyl-1,3-dioxolane

Downstream raw materials:

7-benzyloxy-2-[2-bromomethyl-2-methoxy-tetrahydrofuran-5-yl]-6-methyl-heptan-2-ol

(1RS,4RS,5SR)-4-<5-(Benzyloxy)-4-methylpentyl>-1-methoxy-4-methyl-3,8-dioxabicyclo<3.2.1>octane

(1RS,4SR,5RS)-4-(5-hydroxy-4,8-dimethyl-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo<3.2.1>octane-1-acetic acid