L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone

Base Information

• Chemical Name: L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone
• CAS No.: 158976-98-8
• Molecular Formula: C19H20 O4
• Molecular Weight: 312.36
• Mol file: 158976-98-8.mol

Synonyms:L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone

Chemical Property of L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone

Chemical Property:

• Boiling Point: 474.0±40.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 3.10410

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone

There total 7 articles about L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone 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: 69.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + 2-deoxy-D-ribonolactone-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one (78185-09-8) → 3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone (158976-98-8)

Guidance literature:

With trifluorormethanesulfonic acid; In 1,4-dioxane; at 20 ℃; pH=2.5 - 3;

DOI:10.1080/07328300008544100

Reference yield:

1,3-dibenzyloxy-2-propyl-diazoacetate (158976-92-2) → 3O,5O-dibenzyl-2-deoxy-1,4-xylonolactone (78138-97-3) + 3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone (158976-98-8) + (4R,5S)-4-Benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

Guidance literature:

Rh₂(5R-MEPY)₄; In dichloromethane; for 10h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1016/S0040-4039(00)76684-6

Reference yield:

2,5-di-O-tosyl-D-ribono-1,4-lactone (82130-86-7) → 3,5-di-O-benzyl-2-deoxy-L-threo-pentono-1,4-lactone (158976-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Br₂; hydrazine / H₂O; dioxane / 0 - 20 °C

2: aq. KOH / 20 °C

3: 69 percent / CF₃SO₃H / dioxane / 20 °C / pH 2.5 - 3

With potassium hydroxide; trifluorormethanesulfonic acid; bromine; hydrazine; In 1,4-dioxane; water; 1: Reduction / 2: Hydrolysis / 3: Esterification;

DOI:10.1080/07328300008544100

upstream raw materials:

1,3-dibenzyloxy-2-propyl-diazoacetate

O-benzyl 2,2,2-trichloroacetimidate

2-deoxy-D-ribonolactone-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

(2S,3R)-(3-hydroxy-5-oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

methanesulfonic acid (1S,2S)-2-benzyloxy-1-benzyloxymethyl-4-methanesulfonyloxybutyl ester

N-benzyl-3,5-di-O-benzyl-1,2,4-trideoxy-1,4-imino-D-erythro-pentitol

3,5-di-O-benzyl-1,2,4-trideoxy-1,4-imino-D-erythro-pentitol

(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidinium hydrochloride