(2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin

Base Information

• Chemical Name: (2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin
• CAS No.: 835896-95-2
• Molecular Formula: C₃₃H₃₂O₁₀
• Molecular Weight: 588.611

Synonyms:(2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin

Chemical Property of (2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin

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Technology Process of (2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin

There total 1 articles about (2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin 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: 44.0%

(1S,2S)-trans-1,2-Cyclohexanediol (57794-08-8) + 3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide (82469-69-0) → (2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin (835896-95-2) + (2R,3R,4S,4aR,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin (835896-96-3)

Guidance literature:

With silver carbonate; In dichloromethane; for 3h; Heating;

DOI:10.1002/ejoc.200400457

Reference yield: 65.0%

(2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin (835896-95-2) → (2R,3R,4S,4aR,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin (835896-96-3)

Guidance literature:

In chloroform; at 20 ℃;

DOI:10.1002/ejoc.200400457

Reference yield: 57.0%

(2R,3R,4S,4aS,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin (835896-95-2) → (4aS,5aS,9aS,10aR)-4a-benzoyloxy-2-methyl-octahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one (835653-45-7)

Guidance literature:

With tetrabutylammonium acetate; In chloroform; acetonitrile; at 20 ℃; for 15h;

DOI:10.1002/ejoc.200400457

upstream raw materials:

(1S,2S)-trans-1,2-Cyclohexanediol

3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide

Downstream raw materials:

(4aS,5aS,9aS,10aR)-4a-benzoyloxy-2-methyl-octahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one

(2R,3R,4S,4aR,5aS,9aS,10aR)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-4a-hydroxy-decahydro-2H-pyrano[2,3-b][1,4]benzodioxin

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