(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

Base Information

Chemical Name:(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one
CAS No.:131121-57-8
Molecular Formula:C₂₄H₃₂O₈
Molecular Weight:448.513
Hs Code.:

(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

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Chemical Property of (E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

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Technology Process of (E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

There total 8 articles about (E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one 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: 82.0%

: 131121-23-8
(4R,5R)-5-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 131121-30-7
<α-(benzyloxy)acetyl>methylenetriphenylphosphorane

: 131121-57-8
(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

Guidance literature:: DOI:10.1016/S0040-4039(00)97476-8

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 131121-57-8
(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent

2: 65 percent / NMO / OsO₄, dihydroquinidine p-chlorobenzoate

3: 1) SOCl₂, Et₃N 2) RuCl₃, NaIO₄ / 1) CH₂Cl₂ 2) MeCN, CCl₄, H₂O

4: 2) aq.H₂SO₄ / 1) benzene 2) THF

5: Ba(OMe)2 / methanol

6: PPTS / acetone

7: DIBAH / CH₂Cl₂ / -78 °C

8: 82 percent

With ruthenium trichloride; sodium periodate; thionyl chloride; N-methyl-2-indolinone; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; barium methoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; In methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(00)97476-8

Reference yield:

: 131121-18-1
(E)-ethyl 3-((3aR,4R,6R,6aR)-tetrahydro-4-methoxy-2,2-dimethylfuro[3,4-d][1,3]dioxol-6-yl)acrylate

: 131121-57-8
(E)-1-Benzyloxy-4-[(4S,5S)-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 65 percent / NMO / OsO₄, dihydroquinidine p-chlorobenzoate

2: 1) SOCl₂, Et₃N 2) RuCl₃, NaIO₄ / 1) CH₂Cl₂ 2) MeCN, CCl₄, H₂O

3: 2) aq.H₂SO₄ / 1) benzene 2) THF

4: Ba(OMe)2 / methanol

5: PPTS / acetone

6: DIBAH / CH₂Cl₂ / -78 °C

7: 82 percent

With ruthenium trichloride; sodium periodate; thionyl chloride; N-methyl-2-indolinone; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; barium methoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; In methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(00)97476-8