(2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine
• CAS No.: 1394311-31-9
• Molecular Formula: C₂₄H₂₆O₅
• Molecular Weight: 394.467

Synonyms:(2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine

Chemical Property of (2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine

Chemical Property:

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Technology Process of (2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine

There total 3 articles about (2R,4aR,5aR,10aR)-10-(benzyloxy)-7-methylene-2-phenyloctahydro-4H-pyrano[2',3':5,6]pyrano[3,2-d][1,3]dioxine 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: 45.0%

phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranosyl sulfoxide → (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)

Guidance literature:

With trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -72 ℃; for 2.5h; Overall yield = 70 %; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja307266n DOI:10.1021/ja307266n

Reference yield: 28.0%

2-methallyltrimethylsilane (18292-38-1) + phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranosyl sulfoxide → (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) + 1,5-anhydro-2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-methallyl-β-D-mannitol (1394311-37-5)

Guidance literature:

With trifluoromethylsulfonic anhydride; triphenylmethane; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -72 ℃; for 2.5h; Concentration; Mechanism; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja307266n DOI:10.1021/ja307266n

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

2-methallyltrimethylsilane

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