Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester
CAS No.:635727-23-0
Molecular Formula:C₂₄H₂₈O₆
Molecular Weight:412.483
Hs Code.:

Synonyms:Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

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Chemical Property of Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

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Technology Process of Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

There total 11 articles about Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester 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:

: 635727-22-9
(2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate

: 635727-23-0
Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

Guidance literature:: (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate; With sodium hydrogencarbonate; ozone; In methanol; at -78 ℃;

With sodium tetrahydroborate; In methanol; at 0 ℃;
DOI:10.1002/anie.200352016

Reference yield:

: 635727-03-6
(2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane

: 635727-23-0
Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / 1-methyl-pyrrolidin-2-one / 6 h / 100 °C

2.1: O₃; NaHCO₃ / methanol / -78 °C

2.2: Me₂S / methanol / 0.5 h / 0 °C

3.1: 313 mg / NaBH₄ / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; sodium hydrogencarbonate; ozone; In 1-methyl-pyrrolidin-2-one; methanol;
DOI:10.1055/s-2004-822340

Reference yield:

: 3663-46-5
5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

: 635727-23-0
Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: (COCl)2; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

2.2: aq. NaOH / 0 °C

3.1: trifluoroacetic acid / toluene / -20 - 0 °C

4.1: (COCl)2; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

5.2: aq. NaOH / 0 °C

6.1: iodine; K₂CO₃ / acetonitrile / -30 - -20 °C

7.1: 1-methyl-pyrrolidin-2-one / 100 °C

8.1: O₃; NaHCO₃ / methanol / -78 °C

8.2: NaBH₄ / methanol / 0 °C

With oxalyl dichloride; 4 A molecular sieve; iodine; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; acetonitrile; 1.1: Swern oxidation / 4.1: Swern oxidation;
DOI:10.1002/anie.200352016