Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Base Information

Chemical Name:Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester
CAS No.:131121-25-0
Molecular Formula:C₂₆H₃₂O₁₀
Molecular Weight:504.534
Hs Code.:

Synonyms:Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

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Chemical Property of Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

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Technology Process of Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

There total 10 articles about Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl 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: 79.0%

: 131121-24-9
Acetic acid (2S,3S,3aR,5S,6R,7R,7aR)-3,5,6-triacetoxy-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

: 762-72-1
allyl-trimethyl-silane

: 131121-25-0
Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Guidance literature:: triphenylmethyl perchlorate; at -5 - 0 ℃;
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

: 131121-25-0
Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Guidance literature:: Multi-step reaction with 10 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

With pyridine; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; N-methyl-2-indolinone; Dowex 50W; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; barium methoxide; 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

: 131121-25-0
Acetic acid (2S,3S,3aR,5S,6S,7R,7aR)-3,6-diacetoxy-5-allyl-2-(3-benzyloxy-2-oxo-propyl)-hexahydro-furo[3,2-b]pyran-7-yl ester

Guidance literature:: Multi-step reaction with 9 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

With pyridine; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; N-methyl-2-indolinone; Dowex 50W; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; barium methoxide; triethylamine; osmium(VIII) oxide; dihydroquinidine 4-chlorobenzoate; triphenylmethyl perchlorate; In methanol; dichloromethane; acetone;
DOI:10.1016/S0040-4039(00)97476-8