alpha-D-Glucofuranose, 6-O-[(1,1-dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-

Base Information

• Chemical Name: alpha-D-Glucofuranose, 6-O-[(1,1-dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-
• CAS No.: 106445-04-9
• Molecular Formula: C₂₂H₃₆O₆Si
• Molecular Weight: 424.61
• DSSTox Substance ID: DTXSID701112673
• Mol file: 106445-04-9.mol

Synonyms:106445-04-9;(R)-1-((3aR,5R,6S,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethan-1-ol;alpha-D-Glucofuranose, 6-O-[(1,1-dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-;DTXSID701112673;G66210;6-O-[(1,1-Dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-alpha-D-glucofuranose

Chemical Property of alpha-D-Glucofuranose, 6-O-[(1,1-dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 424.22811540
• Heavy Atom Count: 29
• Complexity: 540

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C(CO[Si](C)(C)C(C)(C)C)O)OCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](CO[Si](C)(C)C(C)(C)C)O)OCC3=CC=CC=C3)C

Technology Process of alpha-D-Glucofuranose, 6-O-[(1,1-dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)-

There total 8 articles about alpha-D-Glucofuranose, 6-O-[(1,1-dimethylethyl)dimethylsilyl]-1,2-O-(1-methylethylidene)-3-O-(phenylmethyl)- 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%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol (106445-04-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1139/v86-296

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol (106445-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / aq. AcOH / 12 h / 20 °C

2: 89 percent / imidazole / CH₂Cl₂ / 1.5 h / 0 °C

With 1H-imidazole; acetic acid; In dichloromethane;

DOI:10.1055/s-2006-926369

Reference yield:

benzyl bromide (100-39-0) → 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol (106445-04-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH, Bu₄NI / tetrahydrofuran / 48 h / Ambient temperature

2: H₂₀, HCl / methanol / 72 h / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

With hydrogenchloride; dmap; water; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/a800486b

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

tert-butyldimethylsilyl chloride

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

6-deoxy-6-phthalimido-5-O-(tert-butyldimethylsilyl)-3-O-benzyl-1,2-O-isopropylidene-D-glucofuranose

methyl 3-O-benzyl-5-C-tert-butyldimethylsilyloxymethyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-(Z)-enofuranosyluronate

(Z)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enoic acid methyl ester