(S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 434343-00-7
• Molecular Formula: C₃₀H₄₀O₆
• Molecular Weight: 496.644
• Mol file: 434343-00-7.mol

Synonyms:(S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane

There total 2 articles about (S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane 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:

ethyl (1R,2S,3R,4S)-3-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-5-oxobicyclo[2.2.1]heptane-2-carboxylate (213816-61-6) → (S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane (434343-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBALH / tetrahydrofuran / -78 °C

With diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1055/s-2002-19778

Reference yield:

benzyl bromide (100-39-0) + (1S,2S,4R,5R,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxymethyl-4-methoxymethoxy-5-methyl-bicyclo[2.2.1]heptan-2-ol → (S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane (434343-00-7)

Guidance literature:

DOI:10.1055/s-2002-19778

Reference yield: 91.0%

(S)-4-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-[1,3]dioxolane (434343-00-7) → (S)-1-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-ethane-1,2-diol

Guidance literature:

With acetic acid; at 60 ℃;

DOI:10.1055/s-2002-19778

upstream raw materials:

benzyl bromide

ethyl (1R,2S,3R,4S)-3-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-5-oxobicyclo[2.2.1]heptane-2-carboxylate

Downstream raw materials:

(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-methanol

(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]heptane-2-carbaldehyde

(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane