(2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester
CAS No.:914649-67-5
Molecular Formula:C₃₃H₄₃NO₆
Molecular Weight:549.708
Hs Code.:

Synonyms:(2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

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Chemical Property of (2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

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Technology Process of (2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

There total 8 articles about (2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-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: 61.0%

: 660391-11-7
(2S,5S)-2-benzyloxymethyl-5-[5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-pentanoyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

: 914649-67-5
(2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

: 660391-03-7
(2S,5S)-2-benzyloxymethyl-5-[(1R)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; n-heptane; at 0 ℃; for 1h;
DOI:10.1002/chem.200600202

Reference yield:

: 660391-17-3
(2S,5S)-(5-benzyloxymethyl-2,5-dihydro-1H-pyrrol-2-yl)-methanol

: 914649-67-5
(2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 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: 65 percent / tetrahydrofuran / 20 °C

5: NaBH₄

With sodium hypochlorite; sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1002/anie.200352857

Reference yield:

: 660390-94-3
[4S,3(1S)]-3-(1-hydroxymethyl-allyl)-4-vinyl-oxazolidin-2-one

: 914649-67-5
(2S,5S)-2-benzyloxymethyl-5-[(1S)-5-{(5R,7R)-1,6-dioxa-spiro[4.5]dec-7-yl}-1-hydroxypentyl]-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 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: 65 percent / tetrahydrofuran / 20 °C

8: NaBH₄

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; dichloromethane; acetone;
DOI:10.1002/anie.200352857