(R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol

Base Information

Chemical Name:(R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol
CAS No.:201678-25-3
Molecular Formula:C₂₃H₂₈O₆
Molecular Weight:400.472
Hs Code.:

Synonyms:(R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol

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Chemical Property of (R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol

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Technology Process of (R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol

There total 1 articles about (R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol 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%

: 100-59-4
phenylmagnesium chloride

: (3aS,4S,6R,6aS)-4-(4-Methoxy-benzyloxy)-2,2-dimethyl-6-oxiranyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 201678-25-3
(R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at -30 ℃;
DOI:10.1016/S0040-4039(97)10468-3

Reference yield:

: 201678-25-3
(R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-phenyl-ethanol

: (2S,3R,4R,5R)-3-Benzoyloxy-2-benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-nonyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: pyridine / CH₂Cl₂ / 1 h / -78 °C

2: NaN₃ / dimethylformamide / 1 h / Ambient temperature

3: LiAlH₄ / tetrahydrofuran / 0 deg C -> room temp., 1 h

4: pyridine, DMAP / 0 deg C -> room temp., 16 h

5: 85 percent / DDQ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

6: 78 percent / PhIO, H₂O, iodine / CH₂Cl₂ / 4 h / Ambient temperature

7: BF₃*OEt₂ / CH₂Cl₂ / -78 deg C, 5 min, then room temp., 50 min; other reag.

8: pyridine / 0 deg C, 15 min, then -> room temp.

9: NaCO₃ / methanol / 0.75 h / Ambient temperature

10: pyridine / 16 h / Ambient temperature

11: 1.) OsO₄, MNO; 2.) H₂O, NaIO₄ / 1.) H₂O, Me₂CO, t-BuOH

12: BuLi / tetrahydrofuran / 0.17 h / -78 °C

13: H₂ / 10percent Pd/C / ethanol / Ambient temperature

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium azide; iodosylbenzene; boron trifluoride diethyl etherate; water; hydrogen; iodine; manganese(II) oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)10468-3