(R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

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Chemical Name:(R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal
CAS No.:333717-25-2
Molecular Formula:C₂₇H₃₄O₈
Molecular Weight:486.562
Hs Code.:

Synonyms:(R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

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Chemical Property of (R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

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Technology Process of (R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

There total 11 articles about (R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal 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: 84.0%

: (1R,2R)-2-Benzyloxy-1-{(4S,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pentane-1,5-diol

: 333717-25-2
(R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo001447t

Reference yield:

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

: 333717-25-2
(R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / NaIO₄ / H₂O; methanol / 1 h / 20 °C

2.1: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

3.1: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

4.1: IDCP / CH₂Cl₂ / 1 h / 20 °C

5.1: 7.8 g / Zn / aq. ethanol / 1 h / Heating

6.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

6.2: 86 percent / aq. H₂O₂; aq. NaOH / 0 °C

7.1: 84 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

With sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; iodonium(di-γ-collidine) perchlorate; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 7.1: Swern oxidation;
DOI:10.1021/jo001447t

Reference yield:

: (3aS,4R,6S,6aS)-4-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 333717-25-2
(R)-4-Benzyloxy-5-{(4R,5S)-5-[methoxy-(4-methoxy-benzyloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-oxo-pentanal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 10.5 g / HCl / H₂O; methanol / 3 h

2.1: 97 percent / NaIO₄ / H₂O; methanol / 1 h / 20 °C

3.1: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

4.1: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

5.1: IDCP / CH₂Cl₂ / 1 h / 20 °C

6.1: 7.8 g / Zn / aq. ethanol / 1 h / Heating

7.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

7.2: 86 percent / aq. H₂O₂; aq. NaOH / 0 °C

8.1: 84 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

With hydrogenchloride; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; iodonium(di-γ-collidine) perchlorate; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 8.1: Swern oxidation;
DOI:10.1021/jo001447t