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

Base Information

• Chemical Name: (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane
• CAS No.: 635727-03-6
• Molecular Formula: C₁₈H₂₃IO₃
• Molecular Weight: 414.283
• Mol file: 635727-03-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane 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: 91.0%

1-[4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol → (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane (635727-03-6) + (2R,4aR,5R,7S)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane

Guidance literature:

With iodine; potassium carbonate; In acetonitrile; at -30 - -20 ℃; for 1h;

DOI:10.1055/s-2004-822340

Reference yield:

(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol (635727-02-5) → (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane (635727-03-6) + (2R,4aR,5R,7S)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane

Guidance literature:

With iodine; potassium carbonate; In acetonitrile; at -30 - -20 ℃;

DOI:10.1002/anie.200352016

Reference yield:

5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane (3663-46-5) → (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane (635727-03-6)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1002/anie.200352016

upstream raw materials:

(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

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

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

(1S)-1-(2,2,5-trimethyl-1,3-dioxan-5-yl)but-3-en-1-ol

Downstream raw materials:

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

(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

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