(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

Base Information

Chemical Name:(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone
CAS No.:408512-59-4
Molecular Formula:C₄₄H₄₆O₈
Molecular Weight:702.844
Hs Code.:

Synonyms:(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

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Chemical Property of (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

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Technology Process of (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

There total 6 articles about (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone 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:

: 248263-72-1
(1R,2R,3S,4R,5S)-3,4-Bis-benzyloxy-1-benzyloxymethyl-5-((S)-2,3-bis-benzyloxy-propoxy)-cyclopentane-1,2-diol

: 408512-59-4
(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In dichloromethane; at 0 ℃; for 0.833333h;
DOI:10.1002/1521-3765(20020104)8:1<240::AID-CHEM240>3.0.CO;2-G

Reference yield:

: (3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((S)-2,3-bis-benzyloxy-propoxy)-tetrahydro-pyran-2-ol

: 408512-59-4
(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.08 h / -60 - 20 °C

3: 2.9 g / SmI₂; tBuOH / tetrahydrofuran / 4 h / -40 °C

4: 67 percent / CH₂Cl₂ / 16 h / Heating

5: 98 percent / K₂CO₃ / methanol / 20 h / 20 °C

6: aq. NaOCl; TEMPO; KBr / CH₂Cl₂ / 0.83 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; samarium diiodide; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium bromide; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation;
DOI:10.1002/1521-3765(20020104)8:1<240::AID-CHEM240>3.0.CO;2-G

Reference yield:

: 248263-71-0
(2R,3R,4S)-2,3,6-Tris-benzyloxy-4-((S)-2,3-bis-benzyloxy-propoxy)-5-oxo-hexanal

: 408512-59-4
(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-3-((S)-2,3-bis-benzyloxy-propoxy)-2-hydroxy-cyclopentanone

Guidance literature:: Multi-step reaction with 4 steps

1: 2.9 g / SmI₂; tBuOH / tetrahydrofuran / 4 h / -40 °C

2: 67 percent / CH₂Cl₂ / 16 h / Heating

3: 98 percent / K₂CO₃ / methanol / 20 h / 20 °C

4: aq. NaOCl; TEMPO; KBr / CH₂Cl₂ / 0.83 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; samarium diiodide; potassium carbonate; potassium bromide; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/1521-3765(20020104)8:1<240::AID-CHEM240>3.0.CO;2-G