isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

Base Information

• Chemical Name: isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• CAS No.: 1394311-34-2
• Molecular Formula: C₃₀H₄₂O₆Si
• Molecular Weight: 526.745
• Mol file: 1394311-34-2.mol

Synonyms:

Chemical Property of isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

There total 4 articles about isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 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:

3-O-benzyl-4,6-O-benzylidene-2-O-[2-(trimethysilylmethyl)allyl]-α-D-mannopyranosyl trichloroacetimidate + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside (1394311-32-0) + isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (1394311-34-2)

Guidance literature:

3-O-benzyl-4,6-O-benzylidene-2-O-[2-(trimethysilylmethyl)allyl]-α-D-mannopyranosyl trichloroacetimidate; With 2,4,6-tri-tert-butylpyrimidine; In toluene; for 3h;

isopropyl alcohol; In dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 3h; Molecular sieve;

DOI:10.1021/jacs.5b06126

Reference yield:

C33H40O6SSi + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside (1394311-32-0) + isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (1394311-34-2)

Guidance literature:

C₃₃H₄₀O₆SSi; With 2,4,6-tri-tert-butylpyrimidine; In toluene; for 3h;

isopropyl alcohol; With oct-1-ene; In dichloromethane; at -72 - 20 ℃; for 2h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -72 ℃;

DOI:10.1021/jacs.5b06126

Reference yield:

phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranosyl sulfoxide + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside (1394311-32-0) + (2R,4aR,5aS,9aR,10R,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine (1394311-30-8) + (2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine (1394311-31-9) + isopropyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (1394311-34-2)

Guidance literature:

phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranosyl sulfoxide; With oct-1-ene; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -72 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

isopropyl alcohol; In dichloromethane; at -72 ℃; for 2.5h; Concentration; Mechanism; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja307266n DOI:10.1021/ja307266n

upstream raw materials:

isopropyl alcohol