(2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Base Information

• Chemical Name: (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one
• CAS No.: 365212-90-4
• Molecular Formula: C₂₃H₃₂O₅
• Molecular Weight: 388.504
• Mol file: 365212-90-4.mol

Synonyms:(2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Chemical Property of (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

There total 14 articles about (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-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:

4-Nitro-benzoic acid (2S,4S,4aR,6R,8aR)-6-allyl-2-(3-benzyloxy-propyl)-4a,6-dimethyl-7-oxo-octahydro-pyrano[3,2-b]pyran-4-yl ester → (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one (365212-90-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; for 2h;

DOI:10.1021/ol016434w

Reference yield:

(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one (365212-89-1) → (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one (365212-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DEAD; PPh₃ / toluene

2: NaOH / tetrahydrofuran; methanol

With sodium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; toluene; 1: Mitsunobu inversion;

DOI:10.1002/chem.200500993

Reference yield:

(2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one (365212-83-5) → (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one (365212-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / H₂O; DDQ / CH₂Cl₂ / 0.5 h / 20 °C

2: DEAD; PPh₃ / toluene / 0.5 h / Heating

3: 36.6 mg / aq. NaOH / methanol; tetrahydrofuran / 2 h

With sodium hydroxide; water; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 2: Mitsunobu reaction;

DOI:10.1021/ol016434w

upstream raw materials:

(2S,4R)-2-(3-Benzyloxy-propyl)-5-methyl-3,4-dihydro-2H-pyran-4-ol

(2S,4R)-2-(3-Benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-5-methyl-3,4-dihydro-2H-pyran

(2R,4aR,6S,8R,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

(2S,4R,4aS,8aR)-2-(3-Benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-4a,6-dimethyl-2,3,4,4a,8,8a-hexahydro-pyrano[3,2-b]pyran

Downstream raw materials:

(2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one

2-allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-(triisopropyl-silanyloxy)-hexahydro-pyrano[3,2-b]pyran-3-one

C₂₈H₄₄O₅Si

[2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane