(2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

Base Information

• Chemical Name: (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane
• CAS No.: 199122-25-3
• Molecular Formula: C₂₇H₃₂O₄
• Molecular Weight: 420.549

Synonyms:(2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

Chemical Property of (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

There total 9 articles about (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[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: 96.0%

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol (69010-01-1) + (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2,3-Bis-benzyloxy-1-benzyloxymethyl-propoxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene (199122-82-2) → 1,3,4-tribenzyloxy-D-erythritol (101703-83-7) + (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane (199122-25-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; Ambient temperature;

DOI:10.1021/ja971881l

Reference yield: 91.0%

(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde (153380-53-1) + (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol (69010-01-1) → (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane (199122-25-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene;

DOI:10.1021/ja971881l

Reference yield: 91.0%

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol (69010-01-1) + {(1S,2R)-3-Benzyloxy-1-benzyloxymethyl-2-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-propoxy}-tert-butyl-diphenyl-silane (199122-87-7) → (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane (199122-25-3) + (2R,3S)-1,4-Bis-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-butan-2-ol

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; Ambient temperature;

DOI:10.1021/ja971881l

upstream raw materials:

(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol

(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2,3-Bis-benzyloxy-1-benzyloxymethyl-propoxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Benzoic acid (1S,2R)-3-benzyloxy-1-benzyloxymethyl-2-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-propyl ester

Downstream raw materials:

(1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-isopropyl-3-methyl-butoxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

(2S,3R)-1,4-Bis-benzyloxy-3-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-butan-2-ol

(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2,3-Bis-benzyloxy-1-benzyloxymethyl-propoxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

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