(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

Base Information

Chemical Name:(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester
CAS No.:194039-22-0
Molecular Formula:C₄₄H₆₃O₁₁P
Molecular Weight:798.951
Hs Code.:

(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

Synonyms:(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

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Chemical Property of (4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

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Technology Process of (4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

There total 21 articles about (4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl 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:

: 131589-37-2
C₂₂H₂₈O₂

: 194039-22-0
(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 1.5 h

2: 1.) LiCl, i-Pr₂NEt / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 6 h

3: 92 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 15 h / 760 Torr

4: pyridine / CH₂Cl₂

5: LiBr / acetone / Heating

6: 1.) t-BuLi, 2.) CeCl₃

7: 95 percent / NaH

8: 75 percent / DDQ, aq. phosphate buffer / CH₂Cl₂; 2-methyl-propan-2-ol / 0.25 h / Ambient temperature

9: 94 percent / Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

10: tetrahydrofuran; pentane / 0.75 h / -78 °C

11: Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

With pyridine; phosphate buffer; cerium(III) chloride; hydrogen; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium bromide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol; pentane;
DOI:10.1021/ja973287h

Reference yield:

: 106357-23-7
(2S,3S,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol

: 194039-22-0
(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: TBAF / tetrahydrofuran / 1 h / Ambient temperature

2: 83 percent / NaH, TBAI / tetrahydrofuran

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 1.5 h

4: 1.) LiCl, i-Pr₂NEt / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 6 h

5: 92 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 15 h / 760 Torr

6: pyridine / CH₂Cl₂

7: LiBr / acetone / Heating

8: 1.) t-BuLi, 2.) CeCl₃

9: 95 percent / NaH

10: 75 percent / DDQ, aq. phosphate buffer / CH₂Cl₂; 2-methyl-propan-2-ol / 0.25 h / Ambient temperature

11: 94 percent / Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

12: tetrahydrofuran; pentane / 0.75 h / -78 °C

13: Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

With pyridine; phosphate buffer; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium bromide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol; pentane;
DOI:10.1021/ja973287h

Reference yield:

: 203925-53-5
(2S,3R,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanal

: 194039-22-0
(4-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) LiCl, i-Pr₂NEt / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 6 h

2: 92 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 15 h / 760 Torr

3: pyridine / CH₂Cl₂

4: LiBr / acetone / Heating

5: 1.) t-BuLi, 2.) CeCl₃

6: 95 percent / NaH

7: 75 percent / DDQ, aq. phosphate buffer / CH₂Cl₂; 2-methyl-propan-2-ol / 0.25 h / Ambient temperature

8: 94 percent / Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

9: tetrahydrofuran; pentane / 0.75 h / -78 °C

10: Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

With pyridine; phosphate buffer; cerium(III) chloride; hydrogen; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium bromide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol; pentane;
DOI:10.1021/ja973287h