(3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one
• CAS No.: 196393-04-1
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 196393-04-1.mol

Synonyms:(3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one

Chemical Property of (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one

There total 4 articles about (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-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: 72.0%

(3S,4S,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3,4-dimethyl-dihydro-furan-2-one (196392-89-9) → (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one (196393-04-1) + (3S,4S,5R)-5-((S)-2-Benzyloxy-1-hydroxy-ethyl)-3,4-dimethyl-dihydro-furan-2-one (196393-00-7)

Guidance literature:

(3S,4S,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3,4-dimethyl-dihydro-furan-2-one; With sodium hydroxide; In ethanol; at 20 ℃; for 2h;

With acetic acid; In ethanol; at 60 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00660-9

Reference yield: 41.0%

(3S,4S,5R)-5-((S)-2-Benzyloxy-1-hydroxy-ethyl)-3,4-dimethyl-dihydro-furan-2-one (196393-00-7) → (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one (196393-04-1)

Guidance literature:

(3S,4S,5R)-5-((S)-2-Benzyloxy-1-hydroxy-ethyl)-3,4-dimethyl-dihydro-furan-2-one; With sodium hydroxide; In ethanol; at 20 ℃;

With acetic acid; In ethanol; at 60 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00660-9

Reference yield:

(E)-(R)-6-Benzyloxy-2,3-dimethyl-hex-4-enoic acid → (3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one (196393-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 24.8 g / ethyl acetate / 0 - 20 °C

2.1: 62 percent / I₂ / acetonitrile / 0 - 20 °C

3.1: aq. NaOH / ethanol / 2 h / 20 °C

3.2: 72 percent / AcOH / ethanol / 1 h / 60 °C

With sodium hydroxide; iodine; In ethanol; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(02)00660-9

upstream raw materials:

(3S,4S,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3,4-dimethyl-dihydro-furan-2-one

(3S,4S,5R)-5-((S)-2-Benzyloxy-1-hydroxy-ethyl)-3,4-dimethyl-dihydro-furan-2-one

Downstream raw materials:

(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

(2S,3S)-3-Benzyloxy-3-((5R,7S,8R,9S,10S)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-2-methyl-propionic acid

C₄₆H₆₀O₈

7-benzyloxy-2-[2-benzyloxy-2-(8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-1-methyl-ethyl]-6-benzyloxymethyl-9-methyl-4,4a,6,7,8,9,10,10a-octahydro-1,5-dioxa-benzocyclooctene