(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde

Base Information

• Chemical Name: (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde
• CAS No.: 1141365-72-1
• Molecular Formula: C₂₆H₃₆O₄Si
• Molecular Weight: 440.655
• Mol file: 1141365-72-1.mol

Synonyms:(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde

Chemical Property of (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde

There total 2 articles about (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde 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: 52.0%

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanethanol (1141365-70-9) → (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde (1141365-72-1)

Guidance literature:

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanethanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - -30 ℃; Inert atmosphere;

DOI:10.1002/anie.200805488

Reference yield: 43.0%

1,1-dimethylethyl (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanacetate (1141365-69-6) → (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde (1141365-72-1) + (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanethanol (1141365-70-9)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; Inert atmosphere;

DOI:10.1002/anie.200805488

Reference yield: 32.0%

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde (1141365-72-1) + allyl bromide (106-95-6) + 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid (186774-95-8) → 2-propenyl (2S,3S,3'aS,4S,5'R)-3',3'a,4,5,5',6'-hexahydro-4-[2-hydroxyethyl]-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate (1141365-48-1) + 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate (1141365-47-0)

Guidance literature:

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde; 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid; In methanol; at 25 ℃; for 60h;

allyl bromide; With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.200805488

upstream raw materials:

1,1-dimethylethyl (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanacetate

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanethanol

Downstream raw materials:

methyl (2S,3S,3'aS,4S,5'R)-3',3'a,4,5,5',6'-hexahydro-8'-hydroxy-4-[2-hydroxyethyl]-3-methyl-5'-pentyl-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

methyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-8'-hydroxy-3-methyl-5'-pentyl-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

2-propenyl (2S,3S,3'aS,4S,5'R)-3',3'a,4,5,5',6'-hexahydro-4-[2-hydroxyethyl]-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate