1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

Base Information

Chemical Name:1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran
CAS No.:117212-73-4
Molecular Formula:C₂₅H₃₄O₆
Molecular Weight:430.541
Hs Code.:

Synonyms:1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

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Chemical Property of 1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

Chemical Property:

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Technology Process of 1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

There total 12 articles about 1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran 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: 87.0%

: 102342-25-6
1α,2α,3β-trihydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

: 77-76-9
2,2-dimethoxy-propane

: 117212-73-4
1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

Guidance literature:: With (+)-10-camphorsulfonic acid; In Cyclopentane; at 50 ℃; for 3h;
DOI:10.1016/S0040-4020(01)87737-1

Reference yield:

: 98-88-4
benzoyl chloride

: 117212-73-4
1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 2,2'-bipyridyl, 1.6M n-butyllithium / 1.) THF, hexane, 10 min, 2.) THF, RT, 15 min then 1h, reflux

2: 60 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 25 °C

3: 56 percent / NaBH₄ / ethanol / 1.5 h / Heating

4: 87 percent / diisopropylamine, 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

5: 1.) osmium tetraoxide, 2.) sodium bisulfite, H₂O, pyridine / 1.) pyridine, 20h, RT, 2.) 3h

6: 87 percent / (+)-10-camphorsulfonic acid / cyclopentane / 3 h / 50 °C

With pyridine; [2,2]bipyridinyl; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; water; sodium hydrogensulfite; (+)-10-camphorsulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; Cyclopentane;
DOI:10.1016/S0040-4020(01)87737-1

Reference yield:

: 117212-74-5
2,3-dehydro-4α-methyl-9β-hydroxydihydroagarofuran

: 117212-73-4
1α,2α-O-isopropylidene-3β-hydroxy-4α-methyl-9β-benzoyloxydihydroagarofuran

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 2,2'-bipyridyl, 1.6M n-butyllithium / 1.) THF, hexane, 10 min, 2.) THF, RT, 15 min then 1h, reflux

2: 60 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 25 °C

3: 56 percent / NaBH₄ / ethanol / 1.5 h / Heating

4: 87 percent / diisopropylamine, 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

5: 1.) osmium tetraoxide, 2.) sodium bisulfite, H₂O, pyridine / 1.) pyridine, 20h, RT, 2.) 3h

6: 87 percent / (+)-10-camphorsulfonic acid / cyclopentane / 3 h / 50 °C

With pyridine; [2,2]bipyridinyl; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; water; sodium hydrogensulfite; (+)-10-camphorsulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; Cyclopentane;
DOI:10.1016/S0040-4020(01)87737-1