(2S,3S,5R)-2-methoxyoxane-3,4,5-triol

Base Information

• Chemical Name: (2S,3S,5R)-2-methoxyoxane-3,4,5-triol
• CAS No.: 5328-63-2
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 2932999099
• Mol file: 5328-63-2.mol

Synonyms:(2S,3S,5R)-2-methoxyoxane-3,4,5-triol;SCHEMBL14817881;NSC 1975;EINECS 226-215-1

Chemical Property of (2S,3S,5R)-2-methoxyoxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 4.16E-05mmHg at 25°C
• Melting Point: 174oC
• Refractive Index: -240 ° (C=7, H2O)
• Boiling Point: 314°Cat760mmHg
• PKA: 13.04±0.70(Predicted)
• Flash Point: 143.7°C
• PSA: 79.15000
• Density: 1.4g/cm³
• LogP: -1.92820
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

98% ^*data from raw suppliers

Methyl b-D-arabinopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1C(C(C(CO1)O)O)O
• Isomeric SMILES: CO[C@@H]1[C@H](C([C@@H](CO1)O)O)O

Technology Process of (2S,3S,5R)-2-methoxyoxane-3,4,5-triol

There total 133 articles about (2S,3S,5R)-2-methoxyoxane-3,4,5-triol 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: 81.4%

methanol (67-56-1) + L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → methyl β-L-arabinopyranoside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,14703-09-4,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5)

Guidance literature:

With hydrogenchloride; for 6h; Reflux;

DOI:10.1080/00397911.2010.520402

Reference yield: 73.2%

methanol (67-56-1) + L-arabinose (5328-37-0) → methyl β-L-arabinopyranoside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,14703-09-4,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 3h;

DOI:10.1248/cpb.47.1717

Reference yield: 64.6%

methanol (67-56-1) + trigoneoside VI → methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6) + methyl xyloside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5,14703-09-4) + methyl L-rhamnopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8,63864-94-8) + spirosta-5,25(27)-diene-3β-ol

Guidance literature:

With hydrogenchloride; for 2.5h; Product distribution; Heating;

DOI:10.3987/COM-97-S(N)52

upstream raw materials:

L-arabinose

L-arabinose dibenzyl dithioacetal

methanol

L-(+)-arabinose

Downstream raw materials:

methyl-(tri-O-benzoyl-β-D-arabinopyranoside)

methyl-(tris-O-methanesulfonyl-β-D-arabinopyranoside)

methyl 3,4-O-isopropylidene-β-D-arabinopyranoside

O¹,O²;O³,O⁴-diisopropylidene-β-D-arabinopyranose

Refernces

• 1、 Ushimaru, Richiro,Liu, Hung-Wen. "Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics". supporting information. . Retrieved 2019/02/14.
• 2、 -. "TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS". Page/Page column 82; 83; 84. . Retrieved 2018/11/10.