1,4-ANHYDRO-L-RIBITOL

Base Information

• Chemical Name: 1,4-ANHYDRO-L-RIBITOL
• CAS No.: 51607-76-2
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.132
• Mol file: 51607-76-2.mol

Synonyms:1,4-ANHYDRO-L-RIBITOL

Chemical Property of 1,4-ANHYDRO-L-RIBITOL

Chemical Property:

• Melting Point: 99 °C
• Boiling Point: 140 °C(Press: 0.1 Torr)
• PKA: 13.72±0.60(Predicted)
• PSA: 69.92000
• Density: 1.453±0.06 g/cm3(Predicted)
• LogP: -1.90070

Purity/Quality:

99% ^*data from raw suppliers

1-Deoxy-D-ribose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Deoxy-D-ribofuranose is used as a rectant in the synthesis and study of fluorobenzene and benzimidazole nucleic-acid analogs and their influence on stability of RNA duplexes.

Technology Process of 1,4-ANHYDRO-L-RIBITOL

There total 53 articles about 1,4-ANHYDRO-L-RIBITOL 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: 100.0%

2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose (14233-62-6,81799-90-8) → 1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9)

Guidance literature:

With hydrogen; palladium dihydroxide;

DOI:10.1080/07328319808004714

Reference yield: 98.0%

1,4-anhydro-2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol (162635-55-4) → 1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9)

Guidance literature:

With trifluoroacetic acid; at 70 ℃; for 2h;

DOI:10.1016/0008-6215(94)00190-1

Reference yield: 95.0%

(3S,4S)-2-(dihydroxymethyl)tetrahydrofuran-3,4-diol → 1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 24h;

DOI:10.1039/c9gc00448c

upstream raw materials:

methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside

Adonitol

2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose

(2R,3R,4S)-3,4-Bis-trimethylsilanyloxy-2-trimethylsilanyloxymethyl-tetrahydro-furan

Downstream raw materials:

2,3,5-tri-O-benzoyl-1-deoxy-D-ribofuranose

Benzoic acid (2R,3S,4S)-3,4-dimethoxy-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2R,3S,4S)-4-methoxy-2-methoxymethyl-tetrahydro-furan-3-yl ester

Benzoic acid (3S,4R,5R)-4-methoxy-5-methoxymethyl-tetrahydro-furan-3-yl ester

Refernces

• 1、 Betchaku, Mii,Cao, Ji,Liu, Lujie,Nakagawa, Yoshinao,Tamura, Masazumi,Tomishige, Keiichi,Yabushita, Mizuho. "Hydrodeoxygenation of C4-C6 sugar alcohols to diols or mono-alcohols with the retention of the carbon chain over a silica-supported tungsten oxide-modified platinum catalyst". supporting information. p. 5665 - 5679. Retrieved 2021/08/16.
• 2、 Brietzke, Andreas,Eickner, Thomas,Jopp, Stefan,Kragl, Udo,Rei?, Melanie,Stein, Florian,Villinger, Alexander,Vogel, Christian. "Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells". . p. 14299 - 14304. Retrieved 2020/04/23.