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

Base Information

• Chemical Name: 1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol
• CAS No.: 114826-80-1
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461

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

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

Chemical Property:

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

There total 4 articles about 1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol 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: 91.0%

(3R,3aR,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-3-hydroxy-hexahydro-cyclopenta[b]furan-2-one (114924-87-7) → 1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol (114826-80-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Heating;

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) → 1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol (114826-80-1)

Guidance literature:

Multi-step reaction with 4 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

4: 91 percent / LiAlH₄ / diethyl ether / Heating

With lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; sulfuric acid; sodium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; 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) → 1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol (114826-80-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 91 percent / LiAlH₄ / diethyl ether / Heating

With lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione

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

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

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

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