UR9Lba3utq

Base Information

• Chemical Name: UR9Lba3utq
• CAS No.: 28713-39-5
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• UNII: UR9LBA3UTQ
• Nikkaji Number: J896.006B
• Mol file: 28713-39-5.mol

Synonyms:UR9LBA3UTQ;28713-39-5;UNII-UR9LBA3UTQ;Tribenoside impurity B [EP];1,2-O-(1-Methylethylidene)-3,5-bis-O-(phenylmethyl)-alpha-D-glucofuranose;3,5-Di-o-benzyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose;alpha-D-Glucofuranose, 1,2-O-(1-methylethylidene)-3,5-bis-O-(phenylmethyl)-;SCHEMBL6275240;TRIBENOSIDE IMPURITY B [EP IMPURITY];.ALPHA.-D-GLUCOFURANOSE, 1,2-O-(1-METHYLETHYLIDENE)-3,5-BIS-O-(PHENYLMETHYL)-;1,2-O-(1-METHYLETHYLIDENE)-3,5-BIS-O-(PHENYLMETHYL)-.ALPHA.-D-GLUCOFURANOSE;3,5-DI-O-BENZYL-1,2-O-(1-METHYLETHYLIDENE)-.ALPHA.-D-GLUCOFURANOSE;(2R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol;(R)-2-(Benzyloxy)-2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

Chemical Property of UR9Lba3utq

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 400.18858861
• Heavy Atom Count: 29
• Complexity: 500

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C(CO)OCC3=CC=CC=C3)OCC4=CC=CC=C4)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](CO)OCC3=CC=CC=C3)OCC4=CC=CC=C4)C
• Uses: 1,2-O-(1-Methylethylidene)-3,5-bis-O-(phenylmethyl)-α-D-glucofuranose is an impurity of Tribenoside (T945630), which is a vasoprotective drug. It’s used in the treatment of hemorrhoids as it has mild anti-inflammatory and wound healing properties.

Technology Process of UR9Lba3utq

There total 18 articles about UR9Lba3utq 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: 80.0%

(3aR,5R,6S,6aR)-6-Benzyloxy-5-[(R)-1-benzyloxy-2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (28713-39-5) + ethyl p-methoxybenzyl sulfide (83318-92-7)

Guidance literature:

With ethanethiol; tin(ll) chloride; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1055/s-1997-990

Reference yield: 76.0%

6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (246162-52-7) → 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (28713-39-5)

Guidance literature:

palladium dichloride; In methanol; at 20 ℃; for 5h;

DOI:10.1080/07328309908544035

Reference yield: 71.0%

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose N,N-butylenehydrazone (182298-39-1) → 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (28713-39-5)

Guidance literature:

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose N,N-butylenehydrazone; With hydrogenchloride; In diethyl ether; at -10 ℃;

With sodium tetrahydroborate; In methanol; diethyl ether; water; at 0 ℃; Further stages.;

DOI:10.1021/jo015711+

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

iodomethylbenzene

(S)-Benzyloxy-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde

Downstream raw materials:

(S)-Benzyloxy-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde

6-O-(2-methylpropanoyl)-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

6-O-butanoyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

6-O-Butanoyl-1,2-O-isopropylidene-α-D-glucofuranose