(2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane

Base Information

• Chemical Name: (2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane
• CAS No.: 835628-22-3
• Molecular Formula: C₃₁H₂₈O₁₁
• Molecular Weight: 576.557

Synonyms:(2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane

Chemical Property of (2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane

Chemical Property:

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Technology Process of (2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane

There total 2 articles about (2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane 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%

acetic anhydride (108-24-7) + (4aS,6R,7R,8S,8aR)-7,8-bis(benzoyloxy)-6-(benzoyloxymethyl)-8a-hydroxy-1,4,5-trioxa-cis-decalin (790277-32-6) → (2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane (835628-22-3)

Guidance literature:

With perchloric acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/ejoc.200400458

Reference yield:

3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide (82469-69-0) → (2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane (835628-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / dimethylformamide / 24 h / 20 °C

2: 94 percent / aq. HClO₄ / CH₂Cl₂ / 0 - 20 °C

With perchloric acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200400458

Reference yield:

(2R,3R,4S,5S,10S)-10-acetoxy-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-1,6,9-trioxaspiro[4,5]decane (835628-22-3) → (2R,3R,4S,5S,10S)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-10-bromo-1,6,9-trioxaspiro[4,5]decane (835628-24-5)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1002/ejoc.200400458

upstream raw materials:

acetic anhydride

(4aS,6R,7R,8S,8aR)-7,8-bis(benzoyloxy)-6-(benzoyloxymethyl)-8a-hydroxy-1,4,5-trioxa-cis-decalin

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

Downstream raw materials:

(2R,3R,4S,5S,10S)-3,4-bis(benzoyloxy)-2-(benzoyloxymethyl)-10-bromo-1,6,9-trioxaspiro[4,5]decane

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