(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

Base Information

Chemical Name:(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
CAS No.:203925-60-4
Molecular Formula:C₄₉H₆₆O₉
Molecular Weight:799.058
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 15 articles about (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 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: 95.0%

: 100-39-0
benzyl bromide

: 194039-20-8
(1S,3S)-1-{(2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-3-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-1-ol

: 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

Guidance literature:: With sodium hydride;
DOI:10.1021/ja973287h

Reference yield:

: 131589-37-2
C₂₂H₂₈O₂

: 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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; cerium(III) chloride; hydrogen; tert.-butyl lithium; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; lithium bromide; palladium dihydroxide; In ethanol; dichloromethane; acetone;
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

: 203925-60-4
(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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; lithium bromide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetone;
DOI:10.1021/ja973287h