methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate

Base Information

• Chemical Name: methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate
• CAS No.: 1159611-54-7
• Molecular Formula: C₇₈H₁₁₆O₁₄Si₃
• Molecular Weight: 1362.03

Synonyms:methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate

Chemical Property of methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate

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Technology Process of methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate

There total 2 articles about methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-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: 93.0%

C78H118O15Si3 (1190429-46-9) → methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate (1159611-54-7)

Guidance literature:

With dmap; acetic anhydride; In dichloromethane; at 60 ℃;

DOI:10.1021/ol900585t

Reference yield: 93.0%

Methyl glyoxylate (922-68-9) + (2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl) tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxydihydro-2H-pyran-3(4H)-one (1159611-53-6) → methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate (1159611-54-7)

Guidance literature:

(2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl) tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxydihydro-2H-pyran-3(4H)-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

Methyl glyoxylate; In tetrahydrofuran; at -78 ℃; for 0.5h;

With dmap; acetic anhydride; In pyridine; dichloromethane; at 60 ℃;

Reference yield: 82.0%

methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate (1159611-54-7) + octanoic acid anhydride (623-66-5) → (2S,3S,6S,E)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethyl silyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylene tetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-ethoxy-4-(2-methoxy-2-oxoethylidene)tetrahydro-2H-pyran-3-yl octanoate (1159611-55-8)

Guidance literature:

methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate; With cerium(III) chloride heptahydrate; In methanol; at -40 - 20 ℃; for 0.25h;

With sodium tetrahydroborate; In methanol; at -40 ℃; for 3h;

octanoic acid anhydride; With dmap; In dichloromethane; at 20 ℃;

upstream raw materials:

C₇₈H₁₁₈O₁₅Si₃

Methyl glyoxylate

(2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl) tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxydihydro-2H-pyran-3(4H)-one

Downstream raw materials:

C₇₈H₁₁₈O₁₄Si₃

(2S,3S,6S,E)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethyl silyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylene tetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-ethoxy-4-(2-methoxy-2-oxoethylidene)tetrahydro-2H-pyran-3-yl octanoate

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