(S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

Base Information

Chemical Name:(S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester
CAS No.:608525-66-2
Molecular Formula:C₂₅H₃₁N₃O₁₂
Molecular Weight:565.534
Hs Code.:

Synonyms:(S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

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Chemical Property of (S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

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Technology Process of (S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

There total 4 articles about (S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester 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: 60.0%

: 608525-64-0
(S)-2-Azido-3-hydroxy-2-methyl-propionic acid benzyl ester

: 439-03-2,439-04-3,439-05-4,2823-44-1,2823-46-3,3934-29-0,4163-44-4,4163-45-5,20409-31-8,23235-96-3,51897-75-7,51897-76-8,51897-77-9,57573-38-3,62561-28-8,126641-47-2
2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose

: 608525-66-2
(S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

Guidance literature:: With TEA; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/S0040-4039(03)01586-7

Reference yield: 50.0%

: 149707-75-5
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

: 608525-64-0
(S)-2-Azido-3-hydroxy-2-methyl-propionic acid benzyl ester

: 608525-66-2
(S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/S0040-4039(03)01586-7

Reference yield:

: 241148-19-6
(R)-2,3-Dihydroxy-2-methyl-propionic acid benzyl ester

: 608525-66-2
(S)-2-Azido-2-methyl-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / SOCl₂ / CCl₄ / 4 h / Heating

2: 77 percent / NaN₃ / dimethylformamide / 12 h / 50 °C

3: 50 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

With thionyl chloride; sodium azide; boron trifluoride diethyl etherate; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)01586-7