(1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

Base Information

Chemical Name:(1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane
CAS No.:143573-32-4
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

Synonyms:(1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

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Chemical Property of (1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

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Technology Process of (1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

There total 7 articles about (1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane 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: 81.0%

: 143573-31-3
(1R,3R,5R,7R,9S,14R)-7-Phenyl-3-trimethylsilylmethyl-2,6,8,11,13-pentaoxatricyclo<9.3.0.0^9,14>tetradecane

: 143573-32-4
(1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; -78 deg C to - 20 deg C then 1 h;
DOI:10.1016/S0040-4020(01)89027-X

Reference yield:

: 61340-09-8
(2S,4R,5R,6S)-4-<(1R)-1,2-dihydroxyethyl>-5-hydroxy-6-hydroxymethyl-2-phenyl-1,3-dioxane

: 143573-32-4
(1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

Guidance literature:: Multi-step reaction with 5 steps

1: NaIO₄ / methanol / 17 h / Ambient temperature

2: HOAc / 4 h / Ambient temperature

3: 1) NaH, 2) tetrabutylammonium chloride / 1) THF, r.t., 1 h, 2) reflux, 2 h

4: 79 percent / p-toluenesulphonic acid monohydrate / CH₂Cl₂; methanol / 1 h / 0 °C

5: 1) SnCl₄ / 1) CH₂Cl₂, -78 deg C, 15 min

With sodium periodate; tetrabutyl-ammonium chloride; tin(IV) chloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)89027-X

Reference yield:

: 141317-08-0
2,4-O-Benzylidene-L-xylose

: 143573-32-4
(1S,3S,5R,6R)-5-<(1R)-1-Hydroxy-3-butenyl>-3-phenyl-2,4,7,9-tetraoxabicyclo<4.4.0>decane

Guidance literature:: Multi-step reaction with 4 steps

1: HOAc / 4 h / Ambient temperature

2: 1) NaH, 2) tetrabutylammonium chloride / 1) THF, r.t., 1 h, 2) reflux, 2 h

3: 79 percent / p-toluenesulphonic acid monohydrate / CH₂Cl₂; methanol / 1 h / 0 °C

4: 1) SnCl₄ / 1) CH₂Cl₂, -78 deg C, 15 min

With tetrabutyl-ammonium chloride; tin(IV) chloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)89027-X