(2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 914649-88-0
• Molecular Formula: C₃₃H₄₅NO₈
• Molecular Weight: 583.722
• Mol file: 914649-88-0.mol

Synonyms:(2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 10 articles about (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl 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: 78.0%

(2R,4R)-2-Benzyloxymethyl-4-((S)-5-(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl-1-hydroxy-pentyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester → (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester (914649-88-0)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 70 ℃; for 5h;

DOI:10.1002/chem.200600202

Reference yield:

(2S,5S)-(5-benzyloxymethyl-2,5-dihydro-1H-pyrrol-2-yl)-methanol (660391-17-3) → (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester (914649-88-0)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. NaHCO₃; Na₂CO₃ / 0 - 20 °C

2: 89 percent / TENPO; aq. KBr; NaOCl / NaHCO₃ / acetone / 0 °C

3: 81 percent / [(benzotriazol-1-yloxy)tripyrrolidinophosphonium]PF₆; EtN(i-Pr)2 / CH₂Cl₂

4: tetrahydrofuran / 20 °C

5: DIBAL-H / diethyl ether / 0 °C

6: CF₃C(O)CH₃; oxone; aq. Na₂CO₃ / acetonitrile / 0 °C

7: aq. CF₃CO₂H / tetrahydrofuran / 65 °C

With Oxone; sodium hypochlorite; 1,1,1-trifluoro-2-propanone; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; acetonitrile;

DOI:10.1002/anie.200352857

Reference yield:

[4S,3(1S)]-3-(1-hydroxymethyl-allyl)-4-vinyl-oxazolidin-2-one (660390-94-3) → (2R,3R,4R,5R)-2-benzyloxymethyl-5-[(1S)-5-{(5S,7S)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxy-pentyl]-3,4-dihydroxy-pyrrolidine-1-carboxylic acid benzyl ester (914649-88-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / NaH; Bu₄NI / tetrahydrofuran / 20 °C

2: 87 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / CH₂Cl₂ / Heating

3: aq, NaOH / ethanol / Heating

4: aq. NaHCO₃; Na₂CO₃ / 0 - 20 °C

5: 89 percent / TENPO; aq. KBr; NaOCl / NaHCO₃ / acetone / 0 °C

6: 81 percent / [(benzotriazol-1-yloxy)tripyrrolidinophosphonium]PF₆; EtN(i-Pr)2 / CH₂Cl₂

7: tetrahydrofuran / 20 °C

8: DIBAL-H / diethyl ether / 0 °C

9: CF₃C(O)CH₃; oxone; aq. Na₂CO₃ / acetonitrile / 0 °C

10: aq. CF₃CO₂H / tetrahydrofuran / 65 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Oxone; sodium hydroxide; sodium hypochlorite; 1,1,1-trifluoro-2-propanone; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; acetonitrile;

DOI:10.1002/anie.200352857

upstream raw materials:

(2S,5S)-(5-benzyloxymethyl-2,5-dihydro-1H-pyrrol-2-yl)-methanol

[4S,3(1S)]-3-(1-hydroxymethyl-allyl)-4-vinyl-oxazolidin-2-one

(3S,6aS)-1,2-dehydro-3-benzyloxymethyl-5-oxapyrrolizidin-4-one

[4S,3(1S)]-3-[1-benzyloxymethyl-allyl]-4-vinyl-oxazolidin-2-one