1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

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Chemical Name:1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol
CAS No.:303752-91-2
Molecular Formula:C₄₆H₆₆O₁₁S
Molecular Weight:827.089
Hs Code.:

Synonyms:1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

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Chemical Property of 1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

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Technology Process of 1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

There total 6 articles about 1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol 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: 73.0%

: 160280-65-9
(2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-yl methanesulfonate

: 303752-87-6
O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

: 303752-91-2
1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -10 ℃; for 0.5h;
DOI:10.1016/S0008-6215(00)00092-6

Reference yield:

: 100-39-0
benzyl bromide

: 303752-91-2
1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

2: 74 percent / NaOAc / PdCl₂ / acetic acid; H₂O

3: 77 percent / DBU / CH₂Cl₂ / 0.67 h / 20 °C

4: 73 percent / TMSOTf / tetrahydrofuran / 0.5 h / -10 °C

With trimethylsilyl trifluoromethanesulfonate; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1: Alkylation / 2: ether cleavage / 3: Substitution / 4: Substitution;
DOI:10.1016/S0008-6215(00)00092-6

Reference yield:

: 3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0
4,6-O-benzylidene-α,β-D-galactopyranose

: 303752-91-2
1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydride / dimethylformamide / 0.5 h / 0 - 20 °C

2: 69 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

3: 74 percent / NaOAc / PdCl₂ / acetic acid; H₂O

4: 77 percent / DBU / CH₂Cl₂ / 0.67 h / 20 °C

5: 73 percent / TMSOTf / tetrahydrofuran / 0.5 h / -10 °C

With trimethylsilyl trifluoromethanesulfonate; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1: Alkylation / 2: Alkylation / 3: ether cleavage / 4: Substitution / 5: Substitution;
DOI:10.1016/S0008-6215(00)00092-6