(1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:676126-73-1
Molecular Formula:C₁₂H₁₄O₄
Molecular Weight:222.241
Hs Code.:

Synonyms:(1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

There total 10 articles about (1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-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: 63.0%

: 676126-71-9
(1R,3S,4R,7R)-7-(p-methoxybenzyloxy)-1-(p-methoxybenzyloxymethyl)-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

: 676126-73-1
(1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1039/b310719a

Reference yield:

: methyl 2-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-(p-methoxybenzyl)-α,β-L-erythro-pentofuranoside

: 676126-73-1
(1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 10 steps

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

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

2.1: 18-crown-6 / dioxane / 12 h / Heating

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

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

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

5.1: aq. AcOH / 12 h / 20 °C

6.1: 74 percent / tetrahydrofuran / 12 h / 20 °C

7.1: 77 percent / Dess-Martin periodinane / CH₂Cl₂ / 12 h / 20 °C

8.1: 22 percent / aq. NaBH₄ / tetrahydrofuran / 0.5 h / 20 °C

9.1: 97 percent / N,N,N',N'-tetramethylazodicarboxamide; PBu₃ / benzene / 12 h / 20 °C

10.1: 63 percent / DDQ; water / CH₂Cl₂ / 4 h / 20 °C

With sodium tetrahydroborate; 18-crown-6 ether; tributylphosphine; diamide; ammonia; water; sodium hydride; Dess-Martin periodane; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; benzene; 6.1: Grignard addition / 9.1: Mitsunobu reaction;
DOI:10.1039/b310719a

Reference yield:

: (1R,3RS,4S,7R)-1-hydroxymethyl-3-methoxy-7-(p-methoxybenzyloxy)-2,5-dioxabicyclo[2.2.1]heptane

: 676126-73-1
(1R,3S,4S,7R)-7-hydroxy-1-hydroxymethyl-3-phenyl-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 7 steps

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

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

2.1: aq. AcOH / 12 h / 20 °C

3.1: 74 percent / tetrahydrofuran / 12 h / 20 °C

4.1: 77 percent / Dess-Martin periodinane / CH₂Cl₂ / 12 h / 20 °C

5.1: 22 percent / aq. NaBH₄ / tetrahydrofuran / 0.5 h / 20 °C

6.1: 97 percent / N,N,N',N'-tetramethylazodicarboxamide; PBu₃ / benzene / 12 h / 20 °C

7.1: 63 percent / DDQ; water / CH₂Cl₂ / 4 h / 20 °C

With sodium tetrahydroborate; tributylphosphine; diamide; water; sodium hydride; Dess-Martin periodane; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; benzene; 3.1: Grignard addition / 6.1: Mitsunobu reaction;
DOI:10.1039/b310719a