(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

Base Information

Chemical Name:(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate
CAS No.:1261423-05-5
Molecular Formula:C₄₁H₆₀O₁₀Si
Molecular Weight:741.007
Hs Code.:

(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

Synonyms:(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

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Chemical Property of (E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

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Technology Process of (E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

There total 20 articles about (E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate 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: 80.0%

: 922-68-9
Methyl glyoxylate

: 1261423-03-3
(2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxydihydro-2H-pyran-3(4H)-one

: 1261423-05-5
(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

Guidance literature:: With potassium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 1h;
DOI:10.1021/ja110198y

Reference yield:

: 1261422-91-6
(E)-5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoic acid

: 1261423-05-5
(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: dmap; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C / Inert atmosphere; Sonication

2.2: 1 h / 0 °C / Inert atmosphere

3.1: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / -5 °C / Inert atmosphere

3.2: 1.25 h / -5 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / -5 - 20 °C / Inert atmosphere

4.2: -5 °C / Inert atmosphere

5.1: 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc / tetrahydrofuran; dichloromethane / 0 °C / Inert atmosphere; Reflux

6.1: magnesium bis(monoperoxyphthalate)hexahydrate; sodium hydrogencarbonate / methanol; dichloromethane; water / 0 °C

6.2: 1 h / 20 °C / Molecular sieve

7.1: potassium carbonate / tetrahydrofuran; methanol / 1 h / 20 °C

With dmap; n-butyllithium; magnesium bis(monoperoxyphthalate)hexahydrate; 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; 4-(dimethylamino)pyridine hydrochloride; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; lead(II) chloride; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 4.1: Wittig reaction / 4.2: Wittig reaction / 5.1: Rainier metathesis reaction / 7.1: Aldol condensation;
DOI:10.1021/ja110198y

Reference yield:

: 76352-72-2
methyl 2,2-dimethyl-4-pentenoate

: 1261423-05-5
(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-3-en-2-yl)-2-methoxy-3-oxodihydro-2H-pyran-4(3H)-ylidene)acetate

Guidance literature:: Multi-step reaction with 10 steps

1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane; water / 4 h / Reflux

2.1: 2,6-di-tert-butyl-4-methylpyridine; silver trifluoromethanesulfonate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: water; sodium hydroxide / ethanol / 15 h / 0 °C

4.1: dmap; 4-(dimethylamino)pyridine hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C / Inert atmosphere; Sonication

5.2: 1 h / 0 °C / Inert atmosphere

6.1: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / -5 °C / Inert atmosphere

6.2: 1.25 h / -5 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / -5 - 20 °C / Inert atmosphere

7.2: -5 °C / Inert atmosphere

8.1: 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc / tetrahydrofuran; dichloromethane / 0 °C / Inert atmosphere; Reflux

9.1: magnesium bis(monoperoxyphthalate)hexahydrate; sodium hydrogencarbonate / methanol; dichloromethane; water / 0 °C

9.2: 1 h / 20 °C / Molecular sieve

10.1: potassium carbonate / tetrahydrofuran; methanol / 1 h / 20 °C

With dmap; N-Bromosuccinimide; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; magnesium bis(monoperoxyphthalate)hexahydrate; 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; water; silver trifluoromethanesulfonate; 4-(dimethylamino)pyridine hydrochloride; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; lead(II) chloride; zinc; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; water; 7.1: Wittig reaction / 7.2: Wittig reaction / 8.1: Rainier metathesis reaction / 10.1: Aldol condensation;
DOI:10.1021/ja110198y