(E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester
CAS No.:131121-31-8
Molecular Formula:C₃₀H₃₈O₁₂
Molecular Weight:590.625
Hs Code.:

Synonyms:

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Chemical Property of (E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

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Technology Process of (E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

There total 12 articles about (E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester 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:

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

: 131121-31-8,131134-97-9
(E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 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

9: 1) Dowex 50W 2) pyridine, DMAP / 1) H₂O

10: 79 percent / trityl perchlorate / -5 - 0 °C

11: 1) disiamylborane 2) H₂O₂, NaOH / 1) THF

12: py*SO₃, DMSO, Et₃N / CH₂Cl₂

With pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; thionyl chloride; N-methyl-2-indolinone; Dowex 50W; sulfuric acid; dihydrogen peroxide; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; barium methoxide; dimethyl sulfoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; triphenylmethyl perchlorate; 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

: 131121-31-8,131134-97-9
(E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 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

8: 1) Dowex 50W 2) pyridine, DMAP / 1) H₂O

9: 79 percent / trityl perchlorate / -5 - 0 °C

10: 1) disiamylborane 2) H₂O₂, NaOH / 1) THF

11: py*SO₃, DMSO, Et₃N / CH₂Cl₂

With pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; thionyl chloride; N-methyl-2-indolinone; Dowex 50W; sulfuric acid; dihydrogen peroxide; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; barium methoxide; dimethyl sulfoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; triphenylmethyl perchlorate; In methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(00)97476-8

Reference yield:

: 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

: 131121-31-8,131134-97-9
(E)-5-[(3S,3aR,5S,6S,7R,7aR)-3,6,7-Triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-5-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent

2: 1) Dowex 50W 2) pyridine, DMAP / 1) H₂O

3: 79 percent / trityl perchlorate / -5 - 0 °C

4: 1) disiamylborane 2) H₂O₂, NaOH / 1) THF

5: py*SO₃, DMSO, Et₃N / CH₂Cl₂

With pyridine; dmap; sodium hydroxide; Dowex 50W; dihydrogen peroxide; sulfur trioxide pyridine complex; bis-(1,2-dimethylpropyl)borane; dimethyl sulfoxide; triethylamine; triphenylmethyl perchlorate; In dichloromethane;
DOI:10.1016/S0040-4039(00)97476-8