L-threo-Hex-4-enuronic acid, 4,5-dideoxy-4-methyl-2,3-O-(1-methylethylidene)-, methyl ester, (4E)- (9CI)

Base Information

• Chemical Name: L-threo-Hex-4-enuronic acid, 4,5-dideoxy-4-methyl-2,3-O-(1-methylethylidene)-, methyl ester, (4E)- (9CI)
• CAS No.: 791130-94-4
• Molecular Formula: C₁₁H₁₆O₅
• Molecular Weight: 228.245
• Mol file: 791130-94-4.mol

Synonyms:L-threo-Hex-4-enuronic acid, 4,5-dideoxy-4-methyl-2,3-O-(1-methylethylidene)-, methyl ester, (4E)- (9CI)

Chemical Property of L-threo-Hex-4-enuronic acid, 4,5-dideoxy-4-methyl-2,3-O-(1-methylethylidene)-, methyl ester, (4E)- (9CI)

Chemical Property:

• PSA: 61.83000
• LogP: 0.82470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-threo-Hex-4-enuronic acid, 4,5-dideoxy-4-methyl-2,3-O-(1-methylethylidene)-, methyl ester, (4E)- (9CI)

There total 5 articles about L-threo-Hex-4-enuronic acid, 4,5-dideoxy-4-methyl-2,3-O-(1-methylethylidene)-, methyl ester, (4E)- (9CI) 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: 90.0%

(E)-3-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester (851089-26-4) → methyl (2E,4S,5R)-4,5-dihydroxy-4,5-O,O-isopropylidene-3-methyl-6-oxohex-2-enoate (791130-94-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -78 - 0 ℃; for 0.5h;

DOI:10.1002/anie.200460259

Reference yield:

(E)-3-[(4S,5R)-5-(Methoxy-methyl-carbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-2-enoic acid methyl ester (851089-24-2) → methyl (2E,4S,5R)-4,5-dihydroxy-4,5-O,O-isopropylidene-3-methyl-6-oxohex-2-enoate (791130-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaBH₄ / methanol / 18 h / 25 °C

2: 90 percent / (COCl)2; dimethyl sulfoxide; Et₃N / 0.5 h / -78 - 0 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In methanol; 2: Swern oxidation;

DOI:10.1002/anie.200460259

Reference yield:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) → methyl (2E,4S,5R)-4,5-dihydroxy-4,5-O,O-isopropylidene-3-methyl-6-oxohex-2-enoate (791130-94-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / Me₃Al / CH₂Cl₂ / 1 h / -15 °C

2: 66 percent / tetrahydrofuran / 1 h / 0 °C

3: toluene / 27 h / Heating

4: 98 percent / NaBH₄ / methanol / 18 h / 25 °C

5: 90 percent / (COCl)2; dimethyl sulfoxide; Et₃N / 0.5 h / -78 - 0 °C

With sodium tetrahydroborate; oxalyl dichloride; trimethylaluminum; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 3: Wittig reaction / 5: Swern oxidation;

DOI:10.1002/anie.200460259

upstream raw materials:

(E)-3-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester

(E)-3-[(4S,5R)-5-(Methoxy-methyl-carbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-2-enoic acid methyl ester

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

(4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide