3-{(2R,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}-propan-1-ol

Base Information

Chemical Name:3-{(2R,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}-propan-1-ol
CAS No.:203925-61-5
Molecular Formula:C₄₁H₅₈O₈
Molecular Weight:678.907
Hs Code.:

3-{(2R,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}-propan-1-ol

Synonyms:3-{(2R,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}-propan-1-ol

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Chemical Property of 3-{(2R,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}-propan-1-ol

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Technology Process of 3-{(2R,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}-propan-1-ol

There total 16 articles about 3-{(2R,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}-propan-1-ol 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: 75.0%

: 203925-60-4
(2R,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-2-[3-(4-methoxy-benzyloxy)-propyl]-7-methylene-octahydro-pyrano[3,2-b]pyran

: 203925-61-5
3-{(2R,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}-propan-1-ol

Guidance literature:: With phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol; for 0.25h; Ambient temperature;
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

: 203925-61-5
3-{(2R,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}-propan-1-ol

Guidance literature:: Multi-step reaction with 10 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

With pyridine; phosphate buffer; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; 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;
DOI:10.1021/ja973287h

Reference yield:

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

: 203925-61-5
3-{(2R,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}-propan-1-ol

Guidance literature:: Multi-step reaction with 7 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

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