(2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

Base Information

• Chemical Name: (2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one
• CAS No.: 936220-96-1
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.305
• Mol file: 936220-96-1.mol

Synonyms:(2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

Chemical Property of (2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

There total 1 articles about (2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one 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:

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (84170-91-2) → (2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (936220-96-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine; dimethyl sulfoxide; for 2h; Ambient temperature;

DOI:10.1021/ja00341a052

Reference yield:

(2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (936220-96-1) → (2R,4aR,6S,7R,8S,8aS)-6-Methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (84170-92-3)

Guidance literature:

With lithium aluminium tetrahydride; In pyridine; at 0 ℃; for 0.5h; Yield given;

DOI:10.1021/ja00341a052

Reference yield:

(2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (936220-96-1) → Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester (84109-54-6)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄ / pyridine / 0.5 h / 0 °C

2: 83 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 75 percent / NBS, BaCO₃ / CCl₄ / 1.5 h / 80 °C

4: Zn / propan-1-ol; H₂O / 0.5 h / 80 °C

5: NaBH₄ / ethanol / 0.5 h / -35 °C

With 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; barium carbonate; zinc; In pyridine; propan-1-ol; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00341a052

upstream raw materials:

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

Downstream raw materials:

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

Benzoic acid (1R,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-vinyl-butyl ester

Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester

tert-Butyl-((2R,4aR,6S,7R,8R,8aS)-6-methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-dimethyl-silane