[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol
CAS No.:866783-38-2
Molecular Formula:C₂₈H₃₈O₈
Molecular Weight:502.605
Hs Code.:

Synonyms:[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

There total 9 articles about [(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol 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: 88.0%

: 866783-37-1
[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-ylmethoxy]-triisopropyl-silane

: 866783-38-2
[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1055/s-2005-871960

Reference yield:

: (3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-ol

: 866783-38-2
[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / pyridine / 5 h / 20 °C

2: 75 percent / TMSOTf / CH₂Cl₂ / 25 h / -78 - -40 °C

3: NaOMe / methanol / 18 h / 20 °C

4: PPTS / benzene / Heating

5: H₂; AcOH / Pd/C / ethanol / 10 h / 20 °C

6: imidazole / dimethylformamide / 3 h / 20 °C

7: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

8: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1055/s-2005-871960

Reference yield:

: Acetic acid (3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methyl-tetrahydro-pyran-2-yl ester

: 866783-38-2
[(2R,3S,4R,5S,6S)-3,4-Bis-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / TMSOTf / CH₂Cl₂ / 25 h / -78 - -40 °C

2: NaOMe / methanol / 18 h / 20 °C

3: PPTS / benzene / Heating

4: H₂; AcOH / Pd/C / ethanol / 10 h / 20 °C

5: imidazole / dimethylformamide / 3 h / 20 °C

6: 98 percent / NaI; NaH / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

7: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1055/s-2005-871960