[(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester

Base Information

• Chemical Name: [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester
• CAS No.: 114826-88-9
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

Synonyms:[(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester

Chemical Property of [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester

There total 4 articles about [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester 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: 73.0%

((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-acetic acid methyl ester → [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester (114826-88-9)

Guidance literature:

With MoO₅*pyridine*HMPA; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

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) → [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester (114826-88-9)

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

4: 73 percent / LDA, MoOPH / tetrahydrofuran / -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) → [(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hydroxy-acetic acid methyl ester (114826-88-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 73 percent / LDA, MoOPH / tetrahydrofuran / -78 - 20 °C

With MoO₅*pyridine*HMPA; lithium diisopropyl amide; In tetrahydrofuran;

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

upstream raw materials:

(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,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarboxylic acid

2-((1R,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-iodo-cyclopentyloxy)-tetrahydro-pyran

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