(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:676126-72-0
Molecular Formula:C₃₈H₃₄O₆
Molecular Weight:586.684
Hs Code.:

Synonyms:(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

There total 16 articles about (1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane 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: 88.0%

: 676126-70-8
(2R,3R,4R)-4-hydroxy-2-[(R)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

: 676126-72-0
(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With tributylphosphine; diamide; In benzene; at 20 ℃; for 12h;
DOI:10.1039/b310719a

Reference yield:

: 109536-51-8,142226-16-2,69940-04-1
1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 676126-72-0
(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 14 steps

1.1: aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

1.2: 87 percent / aq. NaOH / dioxane / 24 h / 20 °C

2.1: 93 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

3.1: 83 percent / aq. HCl / 36 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

5.1: 18-crown-6-ether / CH₂Cl₂; toluene / 12 h / 50 °C

6.1: ammonia / methanol / 24 h / 20 °C

6.2: NaH / dimethylformamide / 12 h / 20 °C

7.1: 18-crown-6 / dioxane / 12 h / Heating

8.1: ammonia / methanol / 12 h / 20 °C

9.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

9.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

10.1: aq. AcOH / 12 h / 20 °C

11.1: magnesium; iodine / tetrahydrofuran / 1 h / 40 °C

11.2: 71 percent / tetrahydrofuran / 12 h / 20 °C

12.1: pyridinium dichromate; 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

13.1: 246 mg / aq. NaBH₄ / tetrahydrofuran / 0.5 h / 20 °C

14.1: 88 percent / N,N,N',N'-tetramethylazodicarboxamide; PBu₃ / benzene / 12 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; 18-crown-6 ether; tributylphosphine; 3 A molecular sieve; diamide; ammonia; iodine; sodium hydride; magnesium; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; benzene; 1.2: Cannizzaro reaction / 11.2: Grignard addition / 14.1: Mitsunobu reaction;
DOI:10.1039/b310719a

Reference yield:

: 115693-78-2,142226-15-1,69940-02-9
1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 676126-72-0
(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-(1-pyrenyl)-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 15 steps

1.1: 82 percent / aq. AcOH / 24 h / 20 °C

2.1: aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

2.2: 87 percent / aq. NaOH / dioxane / 24 h / 20 °C

3.1: 93 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 83 percent / aq. HCl / 36 h / 20 °C

5.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

6.1: 18-crown-6-ether / CH₂Cl₂; toluene / 12 h / 50 °C

7.1: ammonia / methanol / 24 h / 20 °C

7.2: NaH / dimethylformamide / 12 h / 20 °C

8.1: 18-crown-6 / dioxane / 12 h / Heating

9.1: ammonia / methanol / 12 h / 20 °C

10.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

10.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

11.1: aq. AcOH / 12 h / 20 °C

12.1: magnesium; iodine / tetrahydrofuran / 1 h / 40 °C

12.2: 71 percent / tetrahydrofuran / 12 h / 20 °C

13.1: pyridinium dichromate; 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

14.1: 246 mg / aq. NaBH₄ / tetrahydrofuran / 0.5 h / 20 °C

15.1: 88 percent / N,N,N',N'-tetramethylazodicarboxamide; PBu₃ / benzene / 12 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; 18-crown-6 ether; tributylphosphine; 3 A molecular sieve; diamide; ammonia; iodine; sodium hydride; magnesium; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; benzene; 2.2: Cannizzaro reaction / 12.2: Grignard addition / 15.1: Mitsunobu reaction;
DOI:10.1039/b310719a