(1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane
• CAS No.: 110104-50-2
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 110104-50-2.mol

Synonyms:(1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property of (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane

There total 3 articles about (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane 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: 100.0%

benzyl bromide (100-39-0) + (1S,2S,3S,5R)-2-methyl-6,8-dioxabicyclo<3.2.1>octan-3-ol (85433-13-2) → (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane (110104-50-2)

Guidance literature:

With NaBu₄NI; sodium hydride; In tetrahydrofuran; Ambient temperature;

Reference yield:

1,6:3,4-dianhydro-2-O-tosyl-D-galactose (6167-32-4) → (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane (110104-50-2)

Guidance literature:

Multi-step reaction with 3 steps

1: CuI / tetrahydrofuran

2: 80 percent / LiBEt₃H / tetrahydrofuran

3: 94 percent / NaH / n-Bu₄NI

With sodium hydride; lithium triethylborohydride; copper(l) iodide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)85401-5

Reference yield:

(1S,2S,3S,4R,5R)-2-methyl-4-<(p-toluenesulfonyl)-oxy>-6,8-dioxabicyclo<3.2.1>octan-3-ol (85433-11-0) → (1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane (110104-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / LiBEt₃H / tetrahydrofuran

2: 94 percent / NaH / n-Bu₄NI

With sodium hydride; lithium triethylborohydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)85401-5

upstream raw materials:

benzyl bromide

(1S,2S,3S,5R)-2-methyl-6,8-dioxabicyclo<3.2.1>octan-3-ol

1,6:3,4-dianhydro-2-O-tosyl-D-galactose

(1S,2S,3S,4R,5R)-2-methyl-4-<(p-toluenesulfonyl)-oxy>-6,8-dioxabicyclo<3.2.1>octan-3-ol

Downstream raw materials:

2,2-Dimethyl-propionic acid (3R,4R,5R,6S)-3-benzyloxy-5,7-dihydroxy-4,6-dimethyl-heptyl ester

2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester

2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4,6-dimethyl-hept-6-enyl ester

(2S,3S,4R)-4-Benzyloxy-2-isopropenyl-6-methoxy-3-methyl-tetrahydro-pyran