(2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate
• CAS No.: 1334607-25-8
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.401

Synonyms:

Chemical Property of (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate

There total 10 articles about (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate 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,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl pivalate (1334607-07-6) → (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate (1334607-28-1) + (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate (1334607-25-8)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 0 ℃; optical yield given as %de;

DOI:10.1039/c1cc13837e

Reference yield:

1-(2-furyl)ethanol (4208-64-4) → (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate (1334607-28-1) + (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate (1334607-25-8)

Guidance literature:

Multi-step reaction with 9 steps

1: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C

2: dmap / dichloromethane / 12 h / -78 - -30 °C

3: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 8 h / 0 °C

4: dihydrogen peroxide; sodium hydroxide / methanol; water / 6 h / 20 °C

5: hydrazine hydrate / methanol / 0.5 h / 0 °C

6: manganese(IV) oxide / dichloromethane / 12 h / 50 °C

7: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 2 h / -78 °C

8: dmap / dichloromethane / 20 °C / Inert atmosphere

9: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 0 °C

With dmap; manganese(IV) oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; cerium(III) chloride; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; hydrazine hydrate; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; 5: Wharton rearrangement / 5: Wharton rearrangement;

DOI:10.1039/c1cc13837e

Reference yield:

1-(2-furyl)-1-ethanone (1192-62-7,80145-44-4) → (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate (1334607-28-1) + (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate (1334607-25-8)

Guidance literature:

Multi-step reaction with 10 steps

1: (R)-RuCl(η6-mesitylene)-(S,S)-TsDPEN; sodium formate; cetyltrimethylammonim bromide; sodium hydrogencarbonate / dichloromethane; water / 24 h / 20 °C

2: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C

3: dmap / dichloromethane / 12 h / -78 - -30 °C

4: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 8 h / 0 °C

5: dihydrogen peroxide; sodium hydroxide / methanol; water / 6 h / 20 °C

6: hydrazine hydrate / methanol / 0.5 h / 0 °C

7: manganese(IV) oxide / dichloromethane / 12 h / 50 °C

8: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 2 h / -78 °C

9: dmap / dichloromethane / 20 °C / Inert atmosphere

10: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 0 °C

With dmap; manganese(IV) oxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; cerium(III) chloride; (R)-RuCl(η6-mesitylene)-(S,S)-TsDPEN; dihydrogen peroxide; sodium formate; sodium acetate; cetyltrimethylammonim bromide; sodium hydrogencarbonate; hydrazine hydrate; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; 6: Wharton rearrangement / 6: Wharton rearrangement;

DOI:10.1039/c1cc13837e

upstream raw materials:

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

1-(2-furyl)ethanol

1-(2-furyl)-1-ethanone

(1R,2R,4S,6S)-2-(benzyloxy)-4-methyl-3,7-dioxabicyclo[4.1.0]-heptan-5-one

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