(Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

Base Information

Chemical Name:(Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester
CAS No.:885481-08-3
Molecular Formula:C₃₉H₄₃NO₇
Molecular Weight:637.773
Hs Code.:

Synonyms:(Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

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Chemical Property of (Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

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Technology Process of (Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

There total 1 articles about (Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl 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%

: 105-36-2
ethyl bromoacetate

: 113019-41-3
1-Deoxy-2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl cyanide

: 885481-08-3
(Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

Guidance literature:: With zinc; In tetrahydrofuran; Heating;
DOI:10.1055/s-2006-933103

Reference yield:

: 885481-08-3
(Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

: (S)-3-tert-Butoxycarbonylamino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH(OAc)3; glac. AcOH / 1 h / 20 °C

2: aq. NaHCO₃ / dioxane / 12 h / 20 °C

With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; In 1,4-dioxane;
DOI:10.1055/s-2006-933103

Reference yield:

: 885481-08-3
(Z)-3-Amino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acrylic acid ethyl ester

: (R)-3-tert-Butoxycarbonylamino-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH(OAc)3; glac. AcOH / 1 h / 20 °C

2: aq. NaHCO₃ / dioxane / 12 h / 20 °C

With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; In 1,4-dioxane;
DOI:10.1055/s-2006-933103