(2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine
• CAS No.: 68366-59-6
• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 384.386
• Mol file: 68366-59-6.mol

Synonyms:(2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

Chemical Property of (2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[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,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

There total 14 articles about (2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[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: 94.0%

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside (28642-64-0,35823-97-3,38992-99-3,51591-23-2,55169-75-0,56253-26-0,72659-78-0,80041-30-1,80299-59-8,86420-70-4,86420-72-6,91685-06-2,99265-94-8,109010-33-5,118246-05-2,126255-07-0) → (2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine (68366-59-6)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; Reflux;

DOI:10.1021/acs.orglett.5b02849

Reference yield: 80.0%

methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside (86420-70-4) → methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-xylo-hexopyranosid-3-ulose (28642-65-1,38993-04-3,68366-59-6,75879-92-4,109010-31-3,109010-34-6)

Guidance literature:

With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane;

DOI:10.1246/bcsj.54.2379

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → (2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine (68366-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Me₂SnCl₂; K₂CO₃ / tetrahydrofuran / 72 h / 20 °C

2: pyridinium dichromate; 3 Angstroem molecular sieves / CH₂Cl₂ / 24 h / 20 °C

With dipyridinium dichromate; 3 A molecular sieve; dimethyltin dichloride; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2005-918474

upstream raw materials:

methyl 2-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside

benzoyl chloride

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

Downstream raw materials:

methyl 4,6-O-benzylidene-3-C-methyl-α-D-allopyranoside

Methyl-2-O-benzoyl-4,6-O-benzyliden-2-C-2-methyl-α-D-ribo-hexopyranosid-3-ulose

methyl 3-C-allyl-4,6-O-benzylidene-α-D-allopyranoside

ethyl [(3Z)-(methyl 2-O-benzoyl-(R)-4,6-O-benzylidene-3-deoxy-α-D-ribohexopyranosid-3-ylidene)]acetate