(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

Base Information

Chemical Name:(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol
CAS No.:217486-63-0
Molecular Formula:C₃₉H₅₂O₁₀
Molecular Weight:680.836
Hs Code.:

(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

Synonyms:(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

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Chemical Property of (E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

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Technology Process of (E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

There total 6 articles about (E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-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:

: (2R,3S)-9-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-4-ol

: 217486-63-0
(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: NaH / 1,2-dimethoxy-ethane / -78 °C

2: 97 percent / CsF / dimethylformamide / 14 h / 120 °C

3: 90 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.25 h / Ambient temperature

4: 1.) NaH / 1.) hexane, DMSO, RT, 40 min, 2.) hexane, DMSO, RT, 6 d

5: 1.) n-BuLi, 2.) BF₃*OEt₂ / 1.) THF, hexane, -78 deg C, 3 h, 2.) THF, hexane, -78 deg C, 5 h

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; cesium fluoride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja982403t

Reference yield:

: 217486-67-4
[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-methanol

: 217486-63-0
(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.25 h / Ambient temperature

2: 1.) NaH / 1.) hexane, DMSO, RT, 40 min, 2.) hexane, DMSO, RT, 6 d

3: 1.) n-BuLi, 2.) BF₃*OEt₂ / 1.) THF, hexane, -78 deg C, 3 h, 2.) THF, hexane, -78 deg C, 5 h

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; acetonitrile;
DOI:10.1021/ja982403t

Reference yield:

: 217486-29-8
Acetic acid (2R,3S)-9-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-4-yl ester

: 217486-63-0
(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: K₂CO₃, MeOH / 0.42 h

2: NaH / 1,2-dimethoxy-ethane / -78 °C

3: 97 percent / CsF / dimethylformamide / 14 h / 120 °C

4: 90 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.25 h / Ambient temperature

5: 1.) NaH / 1.) hexane, DMSO, RT, 40 min, 2.) hexane, DMSO, RT, 6 d

6: 1.) n-BuLi, 2.) BF₃*OEt₂ / 1.) THF, hexane, -78 deg C, 3 h, 2.) THF, hexane, -78 deg C, 5 h

With methanol; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; cesium fluoride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja982403t