D-erythro-Pentonic acid, 2,3-dideoxy-2-[[(phenylmethoxy)carbonyl]amino]-, gamma-lactone (9CI)

Base Information

• Chemical Name: D-erythro-Pentonic acid, 2,3-dideoxy-2-[[(phenylmethoxy)carbonyl]amino]-, gamma-lactone (9CI)
• CAS No.: 132970-47-9
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.26
• Mol file: 132970-47-9.mol

Synonyms:D-erythro-Pentonic acid, 2,3-dideoxy-2-[[(phenylmethoxy)carbonyl]amino]-, gamma-lactone (9CI)

Chemical Property of D-erythro-Pentonic acid, 2,3-dideoxy-2-[[(phenylmethoxy)carbonyl]amino]-, gamma-lactone (9CI)

Chemical Property:

• PSA: 84.86000
• LogP: 0.98010

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-erythro-Pentonic acid, 2,3-dideoxy-2-[[(phenylmethoxy)carbonyl]amino]-, gamma-lactone (9CI)

There total 9 articles about D-erythro-Pentonic acid, 2,3-dideoxy-2-[[(phenylmethoxy)carbonyl]amino]-, gamma-lactone (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%

(R)-2-Benzyloxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester (132970-39-9) → ((3R,5S)-5-Hydroxymethyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester (132970-47-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 3h; Ambient temperature;

DOI:10.1055/s-1991-26378

Reference yield: 70.0%

((1R,3S)-1-Furan-2-yl-3,4-dihydroxy-butyl)-carbamic acid benzyl ester (181637-39-8) → ((3R,5S)-5-Hydroxymethyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester (132970-47-9)

Guidance literature:

With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 ℃;

DOI:10.1016/0040-4039(96)01365-2 DOI:10.1016/S0040-4020(98)00736-4

Reference yield:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → ((3R,5S)-5-Hydroxymethyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester (132970-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) t-BuOK / 1) -70 deg C, 15 min 2) a) -70 deg C, 0.5 h b) to 35 deg C, 4.5 h

2: 93 percent / H₂ / ⁽¹⁺⁾*BF₄^(1-) / ethanol / 72 h / 2250.2 Torr / Ambient temperature

3: 90 percent / 6N HCl / dioxane / 3 h / Ambient temperature

With hydrogenchloride; potassium tert-butylate; hydrogen; (R,R)-(-)-1,2-bis[(o-methoxy-phenyl)phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In 1,4-dioxane; ethanol;

DOI:10.1055/s-1991-26378

upstream raw materials:

(R)-2-Benzyloxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester

((1R,3S)-1-Furan-2-yl-3,4-dihydroxy-butyl)-carbamic acid benzyl ester

benzyl chloroformate

N-((1R,3S)-1-Furan-2-yl-3,4-dihydroxy-butyl)-4-methyl-benzenesulfonamide

Refernces

• 1、 Liao, Li-Xin,Zhou, Wei-Shan. "A new approach to clavalanine β-lactam antibiotic: Transformation of chiral α-furfuryl amide into the δ-hydroxyl-α-amino lactones via asymmetrical dihydroxylation". . p. 6371 - 6374. Retrieved 2007/10/03.