3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose

Base Information

• Chemical Name: 3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose
• CAS No.: 63593-03-3
• Molecular Formula: C16H22 O6
• Molecular Weight: 310.347
• Hs Code.: 2932990090
• European Community (EC) Number: 613-267-9,691-994-0
• DSSTox Substance ID: DTXSID501120672
• Nikkaji Number: J1.184.116C
• Mol file: 63593-03-3.mol

Synonyms:3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose

Chemical Property of 3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose

Chemical Property:

• Boiling Point: 442.5±45.0 °C(Predicted)
• PKA: 13.95±0.10(Predicted)
• PSA: 77.38000
• Density: 1.29
• LogP: 0.80300
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 310.14163842
• Heavy Atom Count: 22
• Complexity: 375

Purity/Quality:

99%, ^*data from raw suppliers

3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)(CO)CO)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@@H]2[C@@H](C(O[C@@H]2O1)(CO)CO)OCC3=CC=CC=C3)C

Technology Process of 3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose

There total 18 articles about 3-O-Benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-a-D-ribofuranose 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: 94.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (63593-02-2) → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane;

DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 144h;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C16H22O6 → 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3)

Guidance literature:

C₁₆H₂₂O₆; With sodium periodate; In water; at 15 - 30 ℃; for 1h; Large scale;

formaldehyd; With sodium hydroxide; In water; at 30 ℃; for 24h; Temperature; Large scale;

upstream raw materials:

formaldehyd

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

{(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

C₂₂H₃₆O₆Si

Refernces

• 1、 -. "CYCLIC DINUCLEOTIDE COMPOUND AND USES THEREOF". . . Retrieved 2021/11/05.
• 2、 -. "SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF". Paragraph 1083; 1087. . Retrieved 2016/03/08.