(3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one
• CAS No.: 114924-87-7
• Molecular Formula: C₂₂H₂₄O₅
• Molecular Weight: 368.43

Synonyms:(3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one

Chemical Property of (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one

There total 6 articles about (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-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:

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) → (3S,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one (114826-96-9,114924-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) H₂SO₄, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H⁺), 70 deg C, 15 h

2: 60 percent / NaH / dimethylformamide

3: LDA, MoOPH / tetrahydrofuran / 9 h / -78 - 20 °C

With MoO₅*pyridine*HMPA; sulfuric acid; sodium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) → (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one (114924-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) H₂SO₄, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H⁺), 70 deg C, 15 h

2: 60 percent / NaH / dimethylformamide

3: LDA, MoOPH / tetrahydrofuran / 9 h / -78 - 20 °C

With MoO₅*pyridine*HMPA; sulfuric acid; sodium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

(3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one (114826-79-8) → (3S,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one (114826-96-9,114924-87-7) + (3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one (114924-87-7)

Guidance literature:

With MoO₅*pyridine*HMPA; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 9h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(01)91379-6

upstream raw materials:

(3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

Downstream raw materials:

1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol

(1R, 3S, 4R)-1-amino-3-benzyloxy-4-(benzyloxymethyl)cyclopentane

(1R,2S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopentanol

(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

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