(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

Base Information

Chemical Name:(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran
CAS No.:1253890-80-0
Molecular Formula:C₁₈H₂₀O₉
Molecular Weight:380.351
Hs Code.:

Synonyms:(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

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Chemical Property of (-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

Chemical Property:

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Technology Process of (-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

There total 12 articles about (-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran 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: 93.0%

: 1253890-79-7
(-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol

: 108-24-7
acetic anhydride

: 1253890-80-0
(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

Guidance literature:: With pyridine;
DOI:10.1016/j.tet.2010.07.074

Reference yield:

: C₂₆H₂₆O₅

: 1253890-80-0
(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 4 h / 0 °C

2: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; toluene / 3 h / 0 °C

3: tin (IV) chloride pentahydrate / dichloromethane / 0.5 h / 0 °C

4: platinum(IV) oxide; hydrogen / methanol / 2 h / 1551.49 Torr

5: pyridine / 12 h / 0 °C

With pyridine; platinum(IV) oxide; osmium(VIII) oxide; tin (IV) chloride pentahydrate; hydrogen; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 1: |Wittig Olefination;
DOI:10.1016/j.tetlet.2016.12.083

Reference yield:

: 3843-74-1,67667-67-8
Methyl caffeate

: 1253890-80-0
(-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium carbonate / acetone / 15 h / 56 °C / Inert atmosphere

2.1: AD-mix-β; methanesulfonamide / tert-butyl alcohol; water / 12 h / 20 °C

3.1: boron trifluoride diethyl etherate / acetone / 2 h

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere

5.2: 0.33 h / -78 - 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 4 h / 0 °C

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; toluene / 3 h / 0 °C

8.1: tin (IV) chloride pentahydrate / dichloromethane / 0.5 h / 0 °C

9.1: platinum(IV) oxide; hydrogen / methanol / 2 h / 1551.49 Torr

10.1: pyridine / 12 h / 0 °C

With pyridine; platinum(IV) oxide; osmium(VIII) oxide; lithium aluminium tetrahydride; tin (IV) chloride pentahydrate; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; AD-mix-β; hydrogen; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 5.1: |Swern Oxidation / 5.2: |Swern Oxidation / 6.1: |Wittig Olefination;
DOI:10.1016/j.tetlet.2016.12.083