Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (1R,2S,3S,4S)-

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (1R,2S,3S,4S)-
• CAS No.: 78037-77-1
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• DSSTox Substance ID: DTXSID20482581
• Nikkaji Number: J1.501.894A

Synonyms:78037-77-1;Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (1R,2S,3S,4S)-;DTXSID20482581;(1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-diyldimethanol

Chemical Property of Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (1R,2S,3S,4S)-

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C(C2CO)CO
• Isomeric SMILES: C1[C@@H]2C=C[C@H]1[C@@H]([C@H]2CO)CO

Technology Process of Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (1R,2S,3S,4S)-

There total 43 articles about Bicyclo[2.2.1]hept-5-ene-2,3-dimethanol, (1R,2S,3S,4S)- 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%

diethyl (2S,3S)-bicyclo<2.2.1>hept-5-ene-2-endo,3-exo-dicarboxylate (167819-38-7) → (+)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene (78037-77-1,448922-61-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.bmcl.2010.02.038

Reference yield: 95.0%

(1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-((R)-1-anthracen-9-yl-2,2,2-trifluoro-ethyl) ester (929108-82-7) → (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol (53531-34-3,65487-67-4) + (+)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene (78037-77-1,448922-61-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/j.tetasy.2006.11.047

Reference yield: 95.0%

(1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-((S)-1-phenyl-ethyl) ester (162489-30-7) → (+)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene (78037-77-1,448922-61-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/ja00093a013

upstream raw materials:

norbornene-5,6-dicarboxylic acid

(1R,2R)-1-((1R,2R,3R,4S)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-2-((1S,2S,3S,4R)-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-ethane-1,2-diol

cyclopenta-1,3-diene

methyl (E)-4,5,6,7-tetra-O-acetyl-2,3-dideoxy-L-arabino-hept-2-enonate

Downstream raw materials:

Methanesulfonic acid (2R,3R)-3-methanesulfonyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

isoboonein

Acetic acid (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydro-cyclopenta[c]pyran-6-yl ester

(2S,3S)-2,3-bis(p-tolylsulfonyloxymethyl)bicyclo<2.2.1>heptane

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