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

Base Information

• Chemical Name: (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate
• CAS No.: 635727-22-9
• Molecular Formula: C₂₅H₂₈O₅
• Molecular Weight: 408.494
• Mol file: 635727-22-9.mol

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

Chemical Property of (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate

There total 8 articles about (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate 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: 97.0%

sodium benzoate (532-32-1) + (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane (635727-03-6) → (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate (635727-22-9)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 6h;

DOI:10.1055/s-2004-822340

Reference yield:

5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane (3663-46-5) → (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate (635727-22-9)

Guidance literature:

Multi-step reaction with 7 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

With oxalyl dichloride; 4 A molecular sieve; iodine; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In 1-methyl-pyrrolidin-2-one; dichloromethane; toluene; acetonitrile; 1.1: Swern oxidation / 4.1: Swern oxidation;

DOI:10.1002/anie.200352016

Reference yield:

5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde (138517-53-0) → (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate (635727-22-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

1.2: aq. NaOH / 0 °C

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

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

4.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

4.2: aq. NaOH / 0 °C

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

6.1: 1-methyl-pyrrolidin-2-one / 100 °C

With oxalyl dichloride; 4 A molecular sieve; iodine; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In 1-methyl-pyrrolidin-2-one; dichloromethane; toluene; acetonitrile; 3.1: Swern oxidation;

DOI:10.1002/anie.200352016

upstream raw materials:

sodium benzoate

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

5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde

Downstream raw materials:

(2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate

benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

(2R,4S,5S,6R)-4-hydroxy-6-(2-hydroxyethyl)-5-hydroxymethyl-5-methyltetrahydropyran-2-ylmethyl benzoate

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