(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

Base Information

Chemical Name:(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol
CAS No.:163015-31-4
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

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Chemical Property of (1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

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Technology Process of (1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

There total 10 articles about (1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol 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: 71.0%

: 163015-30-3
((1S,2S,6R,7R,8S,9R)-9-Benzyloxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-8-yl)-methanol

: 163015-31-4
(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

Guidance literature:: With hydrogenchloride; In 1,2-dimethoxyethane; at 80 ℃;
DOI:10.1039/c39950000453

Reference yield:

: 144660-40-2
(1S,2R,4R)-3-[1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxycarbonyl)-meth-(Z)-ylidene]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

: 163015-31-4
(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O

2: 98 percent / p-TsOH, CuSO₄

3: 93 percent / DIBAH / CH₂Cl₂ / -78 - 0 °C

4: 70 percent / O₃ / CH₂Cl₂ / -78 °C

5: 92 percent / imidazole / DMAP / CH₂Cl₂

6: 84 percent / L-Selectride / tetrahydrofuran / -78 °C

7: 90 percent / 1percent HCl / ethanol

8: 94 percent / pyridinium toluene-p-sulfonate / toluene / Heating

9: 72 percent / DIBAH / toluene / -78 deg C to r.t.

10: 71 percent / 2 M HCl / 1,2-dimethoxy-ethane / 80 °C

With 1H-imidazole; hydrogenchloride; osmium(VIII) oxide; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; copper(II) sulfate; 4-methylmorpholine N-oxide; dmap; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1039/c39950000453

Reference yield:

: 163015-25-6
2-[(1R,2R,6S,7S,9R)-9-Hydroxymethyl-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-(8E)-ylidene]-ethanol

: 163015-31-4
(1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-diol

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / O₃ / CH₂Cl₂ / -78 °C

2: 92 percent / imidazole / DMAP / CH₂Cl₂

3: 84 percent / L-Selectride / tetrahydrofuran / -78 °C

4: 90 percent / 1percent HCl / ethanol

5: 94 percent / pyridinium toluene-p-sulfonate / toluene / Heating

6: 72 percent / DIBAH / toluene / -78 deg C to r.t.

7: 71 percent / 2 M HCl / 1,2-dimethoxy-ethane / 80 °C

With 1H-imidazole; hydrogenchloride; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; ozone; dmap; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene;
DOI:10.1039/c39950000453