1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone

Base Information

• Chemical Name: 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone
• CAS No.: 29514-28-1
• Molecular Formula: C₉H₁₂O₆
• Molecular Weight: 216.191
• Hs Code.: 2932990090
• Mol file: 29514-28-1.mol

Synonyms:Idofuranuronicacid, 1,2-O-isopropylidene-, g-lactone, b-L-(6CI,8CI); Furo[2',3':4,5]furo[2,3-d]-1,3-dioxole, b-L-idofuranuronic acid deriv.

Chemical Property of 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone

Chemical Property:

• Melting Point: 104-107°C
• PSA: 74.22000
• LogP: -0.85090
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Acetone, Chloroform

Purity/Quality:

95% ^*data from raw suppliers

1,2-O-Isopropylidene-b-L-idofuranosylurono-6,3-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2-O-Isopropylidene-β-L-idofuranurono-6,3-lactone (cas# 29514-28-1) is a compound useful in organic synthesis.

Technology Process of 1,2-O-Isopropylidene--L-idofuranuronic Acid -Lactone

There total 16 articles about 1,2-O-Isopropylidene--L-idofuranuronic Acid -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: 99.0%

L-glucurono-3,6-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetone (67-64-1) → 1,2-O-isopropylidene-α-L-glucurono-3,6-lactone (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1)

Guidance literature:

With sulfuric acid; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2009.08.124

Reference yield: 97.0%

α-D-glucurono-γ-lactone (14362-29-9) + acetone (67-64-1) → D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1)

Guidance literature:

With sulfuric acid; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2008.10.014

Reference yield: 93.0%

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetone (67-64-1) → D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1)

Guidance literature:

With sulfuric acid;

DOI:10.1016/0008-6215(83)88356-6

upstream raw materials:

D-glucurono-6,3-lactone

O¹,O²-isopropylidene-α-D-glucofuranuronic acid

5-O-acetyl-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone

(1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane

Downstream raw materials:

(3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one

(3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol

(1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane

C₁₆H₁₆O₇

Refernces

• 1、 -. "INTERMEDIATES FOR THE PREPARATION OF ERIBULIN THEREOF". Page/Page column 8. . Retrieved 2019/06/11.
• 2、 Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.. "Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities". . p. 2770 - 2779. Retrieved 2014/05/06.