(2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

Base Information

Chemical Name:(2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid
CAS No.:90094-00-1
Molecular Formula:C₃₁H₅₀O₇Si
Molecular Weight:562.819
Hs Code.:

Synonyms:(2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

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Chemical Property of (2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

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Technology Process of (2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

There total 23 articles about (2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid 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: 59.0%

: 90074-16-1
(2R,3R)-2,3-<(R)-(4-methoxybenzylidene)dioxy>-2-methylpentanal

: 90074-15-0
(2R,3S,4S,6R)-3-tert-butyldimethylsilyloxy-8-diethylphosphono-7-oxo-2,4,6-trimethyloctanoic acid

: 90094-00-1
(2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at 0 - 25 ℃; for 13h;
DOI:10.1016/S0040-4039(00)84871-6

Reference yield:

: 90074-06-9
(2S,5S,6S)-2H-5,6-dihydro-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>pyran

: 90094-00-1
(2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: H₂, Et₂O / Rh-Al₂O₃

2: 1) NaH; 2) aq. HCl; 3) Ca(BH₄)2

3: 1) pyridine; 2) imidazole; 3) KOH; 4) DMSO, (COCl)2, Et₃N

4: 2) (COCl)2, DMSO, Et₃N; 3) DDQ; 4) CrO₃, H₂SO₄

5: 59 percent / n-BuLi / tetrahydrofuran / 13 h / 0 - 25 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; n-butyllithium; calcium borohydride; oxalyl dichloride; diethyl ether; sulfuric acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; rhodium on alumina; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)84871-6

Reference yield:

: 108470-06-0
(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

: 90094-00-1
(2R,3S,4S,6R,8E,10S,11R)-3-tert-butyldimethylsilyloxy-10,11-<(R)-(4-methoxybenzylidene)dioxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 1) LiAlH₄; 2) CSA / 1) -20 deg C

2: H₂ / Pd-C / 0 °C

3: 1) NaH; 2) aq. HCl; 3) Ca(BH₄)2

4: 1) pyridine; 2) imidazole; 3) KOH; 4) DMSO, (COCl)2, Et₃N

5: 2) (COCl)2, DMSO, Et₃N; 3) DDQ; 4) CrO₃, H₂SO₄

6: 59 percent / n-BuLi / tetrahydrofuran / 13 h / 0 - 25 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; calcium borohydride; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)84871-6