3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

Base Information

Chemical Name:3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose
CAS No.:271243-81-3
Molecular Formula:C₃₀H₃₆N₃O₈P
Molecular Weight:597.605
Hs Code.:

Synonyms:3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

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Chemical Property of 3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

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Technology Process of 3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

There total 1 articles about 3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose 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: 35.0%

: 160701-84-8
(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 756-79-6
dimethyl methane phosphonate

: 271243-81-3
3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

Guidance literature:: dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.333333h;

(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -70 - -40 ℃; for 1h;
DOI:10.1016/S0957-4166(99)00477-2

Reference yield: 55.0%

: 271243-81-3
3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

: 271243-83-5
2,6-anhydro-3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol

Guidance literature:: With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.75h;
DOI:10.1016/S0957-4166(99)00477-2

Reference yield:

: 271243-81-3
3-azido-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-α-D-galacto-2-heptulopyranose

: ((2R,3R,4R,5R,6R)-3-Amino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 55 percent / triethylsilane; trimethylsilyl triflate / CH₂Cl₂ / 0.75 h / 20 °C

2: H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 2 h / 20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; hydrogen; palladium dihydroxide; In dichloromethane; ethyl acetate; 1: Reduction / 2: Catalytic hydrogenation;
DOI:10.1016/S0957-4166(99)00477-2