Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester
CAS No.:308815-88-5
Molecular Formula:C₃₈H₃₉NO₁₀
Molecular Weight:669.728
Hs Code.:

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl 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: 86.0%

: 308815-87-4
[4-((2S,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2-nitro-phenoxy]-acetic acid

: 308815-88-5
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: [4-((2S,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2-nitro-phenoxy]-acetic acid; With dmap; poly(ethylene glycol) methyl ether; In dichloromethane;

With tin(II) benzenethiolate; thiophenol; triethylamine; In benzene;

Reference yield: 47.0%

: 308815-87-4
[4-((2S,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2-nitro-phenoxy]-acetic acid

: Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

: 308815-88-5
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: [4-((2S,3S,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-2-nitro-phenoxy]-acetic acid; With dmap; poly(ethylene glycol) methyl ether; In dichloromethane;

With samarium diiodide; In tetrahydrofuran; methanol;

Reference yield:

: 3011-34-5
4-hydroxy-3-nitrobenzaldehyde

: 308815-88-5
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: K₂CO₃ / acetonitrile

2.1: NaBH₄ / ethanol

3.1: 92 percent / TMSOTf / CH₂Cl₂

4.1: 100 percent / TFA / CH₂Cl₂

5.1: poly(ethylene glycol) methyl ether; WSCDI; DMAP / CH₂Cl₂

5.2: 32 percent / SmI₂ / methanol; tetrahydrofuran

With dmap; sodium tetrahydroborate; poly(ethylene glycol) methyl ether; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile; 1.1: Alkylation / 2.1: Reduction / 3.1: glycosylation / 4.1: Substitution / 5.1: Solid phase reaction / 5.2: Solid phase reaction;