4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

Base Information

• Chemical Name: 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone
• CAS No.: 498554-12-4
• Molecular Formula: C₂₅H₄₀O₇Si₂
• Molecular Weight: 508.759
• Mol file: 498554-12-4.mol

Synonyms:4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

Chemical Property of 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

There total 3 articles about 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone 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:

(5aS,5bR,7R,9aR,11aR)-11-(allyloxy)-2,2,4,4-tetraisopropyl-7-phenylhexahydro[1,3]dioxino[4',5':5,6]pyrano[3,4-f] [1,3,5,2,4]trioxadisilepine (784157-61-5) → 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone (498554-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃Al / [NiCl₂(dpp)] / toluene / 0 - 24 °C

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With oxalyl dichloride; triethylaluminum; dimethyl sulfoxide; triethylamine; [NiCl₂(dpp)]; In dichloromethane; toluene; 2: Swern oxidation;

DOI:10.1016/j.tetlet.2004.07.145

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone (498554-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 23 °C

2: 99 percent / Et₃Al / [NiCl₂(dpp)] / toluene / 0 - 24 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 1H-imidazole; oxalyl dichloride; triethylaluminum; dimethyl sulfoxide; triethylamine; [NiCl₂(dpp)]; In dichloromethane; N,N-dimethyl-formamide; toluene; 3: Swern oxidation;

DOI:10.1016/j.tetlet.2004.07.145

Reference yield:

(2R,4aR,6aR,11aS,11bR)-8,8,10,10-Tetraisopropyl-2-phenyl-6-[((E)-propenyl)oxy]-hexahydro-1,3,5,7,9,11-hexaoxa-8,10-disila-cyclohepta[a]naphthalene → 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone (498554-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.57 g / HgCl₂; HgO; H₂O / acetone / 1 h / 25 °C

2: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With oxalyl dichloride; water; dimethyl sulfoxide; triethylamine; mercury dichloride; mercury(II) oxide; In dichloromethane; acetone; 2: Swern oxidation;

DOI:10.1016/S0040-4020(02)01329-7

upstream raw materials:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

(5aS,5bR,7R,9aR,11aR)-11-(allyloxy)-2,2,4,4-tetraisopropyl-7-phenylhexahydro[1,3]dioxino[4',5':5,6]pyrano[3,4-f] [1,3,5,2,4]trioxadisilepine

Downstream raw materials:

(1S,2R,4R,7R,10R)-12,12,14,14-tetraisopropyl-9-methylene-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadecane

(5aS,5bR,7R,9aR,11aR)-11-allyl-2,2,4,4-tetraisopropyl-7-phenylhexahydro[1,3]dioxino[4',5':5,6]pyrano[3,4-f][1,3,5,2,4]trioxadisilepin-11-ol

(2R,4aR,5aS,10aS,11R,11aR)-11-(4-Bromo-benzyloxy)-2-naphthalen-2-yl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine