(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 898552-07-3
• Molecular Formula: C₂₉H₃₂O₅
• Molecular Weight: 460.57
• Mol file: 898552-07-3.mol

Synonyms:(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 1 articles about (2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 100.0%

benzyl bromide (100-39-0) + (2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (440333-93-7) → (2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (898552-07-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; for 15h;

DOI:10.1016/j.tetlet.2006.04.018

Reference yield: 100.0%

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (898552-07-3) → (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol (898552-08-4)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; for 18h;

DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (898552-07-3) → (2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol (898552-21-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / p-TsOH*H₂O / tetrahydrofuran; methanol; H₂O / 18 h

2.1: 2,6-lutidine / CH₂Cl₂ / 1.5 h

3.1: CSA / methanol / 2 h

4.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

5.1: MeLi / tetrahydrofuran / 3 h / -78 - -10 °C

6.1: 88 percent / TBAF / tetrahydrofuran / 0.5 h

7.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / 1 h / -20 °C

7.2: 93 percent / PPTS / CH₂Cl₂ / 1 h

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methyllithium; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; water; 4.1: Swern oxidation / 7.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.04.018

upstream raw materials:

benzyl bromide

(2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Downstream raw materials:

(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol

(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde

(2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol