Methyl 3,5-di-O-benzyl-alpha-D-erythro-pentofuranosid-2-ulose

Base Information

• Chemical Name: Methyl 3,5-di-O-benzyl-alpha-D-erythro-pentofuranosid-2-ulose
• CAS No.: 885592-69-8
• Molecular Formula: C20H22O5
• Molecular Weight: 342.392
• DSSTox Substance ID: DTXSID60705468
• Nikkaji Number: J2.493.991J
• Wikidata: Q82638341
• Mol file: 885592-69-8.mol

Synonyms:885592-69-8;Methyl 3,5-di-O-benzyl-alpha-D-erythro-pentofuranosid-2-ulose;(2S,4R,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-one;alpha-D-erythro-Pentofuranosid-2-ulose, methyl 3,5-bis-O-(phenylmethyl)-;(2S,4R,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one;Methyl 3,5-di-O-benzyl-2-keto-alpha-D-ribofuranoside;SCHEMBL264794;DTXSID60705468;NAOWUVUWHAHQNJ-RLLQIKCJSA-N;A861743;1-O-Methyl-2-deoxy-2-oxo-3-O,5-O-dibenzyl-alpha-D-ribofuranose;(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxyoxolane-3-one

Chemical Property of Methyl 3,5-di-O-benzyl-alpha-D-erythro-pentofuranosid-2-ulose

Chemical Property:

• Boiling Point: 483.5±45.0 °C(Predicted)
• PSA: 53.99000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 2.72900
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 342.14672380
• Heavy Atom Count: 25
• Complexity: 401

Purity/Quality:

97% ^*data from raw suppliers

α-D-erythro-Pentofuranosid-2-ulose,methyl3,5-bis-O-(phenylmethyl)- 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(=O)C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3
• Isomeric SMILES: CO[C@@H]1C(=O)[C@@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3

Technology Process of Methyl 3,5-di-O-benzyl-alpha-D-erythro-pentofuranosid-2-ulose

There total 7 articles about Methyl 3,5-di-O-benzyl-alpha-D-erythro-pentofuranosid-2-ulose 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: 97.0%

(2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol (80795-53-5) → (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one (885592-69-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ol071075b

Reference yield:

methyl 2,3,5-tri-O-benzyl-D-ribofuranoside (64363-77-5) → (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one (885592-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tin(IV) chloride / CH₂Cl₂ / 48 h / 0 - 4 °C

2: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

With tin(IV) chloride; Dess-Martin periodane; In dichloromethane;

DOI:10.1021/ol071075b

Reference yield:

methyl ribofuranoside (1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7) → (2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one (885592-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride; tetrabutylammonium iodide / dimethylformamide / 3 h / 20 °C

2: tin(IV) chloride / CH₂Cl₂ / 48 h / 0 - 4 °C

3: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

With tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol071075b

upstream raw materials:

(2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol

methyl ribofuranoside

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

benzyl chloride

Downstream raw materials:

methyl 3,5-di-O-benzyl-2-C-β-methoxymethyl-α-D-ribofuranoside

C₂₂H₂₈O₅

C₃₇H₃₄ClNO₇

C₃₆H₃₀ClNO₆

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