2-O,4-O-[(R)-Ethylidene]-D-erythrose

Base Information

• Chemical Name: 2-O,4-O-[(R)-Ethylidene]-D-erythrose
• CAS No.: 70377-89-8
• Molecular Formula: C6H10O4
• Molecular Weight: 146.143
• DSSTox Substance ID: DTXSID90449106
• Nikkaji Number: J654.437A
• Wikidata: Q82268453
• Mol file: 70377-89-8.mol

Synonyms:70377-89-8;2-O,4-O-[(R)-Ethylidene]-D-erythrose;SCHEMBL17679810;DTXSID90449106;AG-G-74781

Chemical Property of 2-O,4-O-[(R)-Ethylidene]-D-erythrose

Chemical Property:

• PSA: 55.76000
• LogP: -0.69240
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 146.05790880
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1OCC(C(O1)C=O)O
• Isomeric SMILES: C[C@@H]1OC[C@H]([C@@H](O1)C=O)O

Technology Process of 2-O,4-O-[(R)-Ethylidene]-D-erythrose

There total 8 articles about 2-O,4-O-[(R)-Ethylidene]-D-erythrose 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: 96.0%

(1’R)-(-)-4,6-O-ethylidene-D-glucose (13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,18465-50-4,87068-63-1) → (1'R)-(-)-2,4-O-ethylidene-D-erythrose (70377-89-8,315216-23-0)

Guidance literature:

With sodium periodate; sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1021/ol0630651

Reference yield:

O4,O6-((S)-ethylidene)-L-glucose (112246-57-8) → O2,O4-((S)-ethyliden)-L-erythrose (24871-55-4,70377-89-8,87068-62-0,315216-23-0)

Guidance literature:

With sodium periodate; water; sodium hydrogencarbonate;

DOI:10.1021/ja01156a002

Reference yield:

→ (1'R)-(-)-2,4-O-ethylidene-D-erythrose (70377-89-8,315216-23-0)

Guidance literature:

With sodium periodate; water; sodium hydrogencarbonate;

DOI:10.1021/ja01627a053 DOI:10.1021/ja01494a048

upstream raw materials:

4,6-O-ethylidene-D-glucopyranose

(1’R)-(-)-4,6-O-ethylidene-D-glucose

4,6-O-ethylidene-D-glucose

O⁴,O⁶-((S)-ethylidene)-L-glucose

Downstream raw materials:

2,4-di-O-acetyl-3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-allonamide

2,4-di-O-acetyl-3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-mannonamide

2,3-anhydro-N,N-dibenzyl-5-O-benzyl-4,6-O-ethylidene-D-altro-hexonamide

3,6-anhydro-5-O-benzyl-N,N-dibenzyl-D-allonamide

Refernces

• 1、 Clark, J. Stephen,Grainger, Damian M.,Ehkirch, Alexandra A.-C.,Blake, Alexander J.,Wilson, Claire. "Synthesis of the fused polyether core of hemibrevetoxin B by two-directional ring-closing metathesis". . p. 1033 - 1036. Retrieved 2007/10/03.
• 2、 Li, Lian-Sheng,Wu, Yu-Lin,Wu, Yikang. "Total synthesis of fully acetylated N-acetylneuraminic acid (Neu5Ac), 2-deoxy-β-Neu5Ac, and 4-epi-2-deoxy-β-Neu5Ac from D-glucose". . p. 891 - 894. Retrieved 2007/10/03.