beta-D-erythro-Pentopyranoside, methyl 2-deoxy-

Base Information

• Chemical Name: beta-D-erythro-Pentopyranoside, methyl 2-deoxy-
• CAS No.: 17676-20-9
• Molecular Formula: C6H12O4
• Molecular Weight: 148.159
• NSC Number: 90994
• DSSTox Substance ID: DTXSID50938849
• Mol file: 17676-20-9.mol

Synonyms:6-methoxyoxane-3,4-diol;17676-20-9;beta-D-erythro-Pentopyranoside, methyl 2-deoxy-;.beta.-D-erythro-Pentopyranoside, methyl 2-deoxy-;Decitabine Impurity 4 (Methyl 2-deoxy-beta-D-Ribopyranoside);Methyl 2-deoxypentopyranoside;NSC90994;NCIOpen2_001410;D-erythro-Pentopyranoside, methyl 2-deoxy-, .beta.-;SCHEMBL8516120;Methyl 2-deoxypentopyranoside #;DTXSID50938849;CYLGOSOYSUHPCY-UHFFFAOYSA-N;D-erythro-Pentopyranoside, .beta.-;NSC-90994;.alpha.,.beta.-Methyl-2-deoxy-D-ribopyranoside

Chemical Property of beta-D-erythro-Pentopyranoside, methyl 2-deoxy-

Chemical Property:

• Vapor Pressure: 0.000843mmHg at 25°C
• Boiling Point: 271.4°Cat760mmHg
• Flash Point: 117.9°C
• Density: 1.24g/cm³
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 148.07355886
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1CC(C(CO1)O)O

Technology Process of beta-D-erythro-Pentopyranoside, methyl 2-deoxy-

There total 16 articles about beta-D-erythro-Pentopyranoside, methyl 2-deoxy- 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%

methyl 2-deoxy-3,4-O-isopropylidene-β-D-erythro-pentopyranoside (66851-41-0) → methyl 2-deoxy-β-D-erythro-pentopyranoside (17676-20-9)

Guidance literature:

With acetic acid; at 20 ℃; for 20h;

DOI:10.1016/0008-6215(85)85033-3

Reference yield:

methanol (67-56-1) + 2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → methyl 2-deoxy-α-D-erythro-pentopyranoside (6160-56-1) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) + methyl 2-deoxy-β-D-erythro-pentopyranoside (17676-20-9)

Guidance literature:

With hydrogenchloride; for 15h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00121a039

Reference yield:

methyl 3,4-O-isopropylidene-β-D-ribopyranoside (38088-60-7,817620-70-5) → methyl 2-deoxy-β-D-erythro-pentopyranoside (17676-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) 4M NaOH / 1) DMSO, 10 to 20 deg C, 10 min, 2) DMSO, 10 to 20 deg C, 25 min

2: 74 percent / Bu₃SnH, AIBN / benzene / Heating

3: 100 percent / 80percent AcOH / 20 h / 20 °C

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic acid; In benzene;

DOI:10.1016/0008-6215(85)85033-3

upstream raw materials:

1-O-methyl-2-deoxy-D-ribofuranoside

(1R,2R,5R,6R)-2-Methoxy-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

methyl-(2-bromo-2-deoxy-β-D-arabinopyranoside)

methyl 2-deoxy-3,4-O-isopropylidene-β-D-erythro-pentopyranoside

Downstream raw materials:

methyl-[bis-O-(toluene-4-sulfonyl)-β-D-erythro-2-deoxy-pentopyranoside]

BPh(Me-β-D-ery-dPenp3,4H-2)

3-(4-Bromo-phenyl)-1-((3S,4S,6R)-4,6-dimethoxy-tetrahydro-pyran-3-yl)-1-isopropyl-urea

methyl 2-deoxy-α-D-threo-pentopyranoside

Refernces

• 1、 Crotti,Di Bussolo,Favero,Macchia,Pineschi. "An efficient stereoselective synthesis of the amino sugar component (E ring) of calicheamicin γ1(I)". . p. 779 - 786. Retrieved 2007/10/03.
• 2、 Medonos, Ivan,Kocikova, Veroslava,Stanek, Jan,Zobacova, Alena,Jary, Jiri. "METHYL ETHERS OF METHYL 2-DEOXY-α- AND β-D-threo-PENTOPYRANOSIDE". . p. 1671 - 1677. Retrieved 2007/10/02.