Benzyl 2,3-O-Isopropylidene-alpha-D-mannofuranoside

Base Information

• Chemical Name: Benzyl 2,3-O-Isopropylidene-alpha-D-mannofuranoside
• CAS No.: 20689-03-6
• Molecular Formula: C16H22O6
• Molecular Weight: 310.34200
• Nikkaji Number: J82.997H
• Mol file: 20689-03-6.mol

Synonyms:20689-03-6;Benzyl 2,3-O-Isopropylidene-alpha-D-mannofuranoside;Benzyl 2,3-O-Isopropylidene-a-D-mannofuranoside;alpha-D-Mannofuranoside, phenylmethyl 2,3-O-(1-methylethylidene)-;(1R)-1-[(3aS,4S,6R,6aS)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethane-1,2-diol;SCHEMBL10573975;Benzyl 2,3-O-Isopropylidene-?-D-mannofuranoside;W-201807;(1R)-1-[(3aS, 4S, 6R, 6aS)-2, 2-dimethyl-4-phenylmethoxy-3a, 4, 6, 6a-tetrahydrofuro[3, 4-d][1, 3]dioxol-6-yl]ethane-1, 2-diol

Chemical Property of Benzyl 2,3-O-Isopropylidene-alpha-D-mannofuranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 81 - 82 °C
• Boiling Point: 468.846oC at 760 mmHg
• Flash Point: 237.349oC
• PSA: 77.38000
• Density: 1.295g/cm3
• LogP: 0.80140
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in chloroform, dichloromethane or DMSO
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 310.14163842
• Heavy Atom Count: 22
• Complexity: 368

Purity/Quality:

98%Min ^*data from raw suppliers

Benzyl2,3-O-Isopropylidene-α-D-mannofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Benzyl 2,3-O-Isopropylidene-alpha-D-mannofuranoside

There total 9 articles about Benzyl 2,3-O-Isopropylidene-alpha-D-mannofuranoside 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: 93.0%

Acetic acid (R)-2-acetoxy-1-((3aS,4R,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester (77988-67-1) → 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose (74912-02-0,79940-48-0,94118-99-7,20689-03-6)

Guidance literature:

With lithium aluminium tetrahydride;

Reference yield: 59.0%

Acetic acid (3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (16713-80-7,26775-14-4,29474-72-4,29586-98-9,38166-65-3,38166-66-4,38166-68-6,38166-69-7,98032-70-3,98975-57-6) + benzyl alcohol (100-51-6,185532-71-2) → 1-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol (20689-03-6,74912-02-0,79940-48-0,94118-99-7)

Guidance literature:

With hydrogenchloride; acetone; In acetone; at 20 - 60 ℃;

DOI:10.1039/c39900000765

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose (74912-02-0,79940-48-0,94118-99-7,20689-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / NaH / dimethylformamide

2: 100 percent / 70 percent aq. AcOH / 20 °C

With sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(03)00690-7

upstream raw materials:

Acetic acid (3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

benzyl alcohol

Acetic acid (R)-2-acetoxy-1-((3aS,4R,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester

benzyl bromide

Downstream raw materials:

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

(3aR,4S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid

phenylmethyl-2,3-O-(1-methylethylidene)-5,6-O-(N,N-dimethylaminomethylene)-α-D-mannofuranoside

benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride

Refernces

• 1、 Matassini, Camilla,Mirabella, Stefania,Goti, Andrea,Cardona, Francesca. "Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines". . p. 3920 - 3924. Retrieved 2012/09/08.
• 2、 Sato, Ken-Ichi,Akai, Shoji,Hiroshima, Toshiyuki,Aoki, Hidenori,Sakuma, Mayumi,Suzuki, Ken-Ju. "Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN". . p. 3513 - 3516. Retrieved 2007/10/03.