(S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

Base Information

Chemical Name:(S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester
CAS No.:194668-86-5
Molecular Formula:C₃₉H₄₃N₃O₇
Molecular Weight:665.786
Hs Code.:

Synonyms:(S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

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Chemical Property of (S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

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Technology Process of (S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

There total 6 articles about (S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl 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: 92.0%

: 194668-84-3
(R)-2-(Diphenoxy-phosphoryloxy)-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

: 194668-86-5
(S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

Guidance literature:: With tetrabutylammoniun azide; In toluene; at 55 ℃;
DOI:10.1039/a703063k

Reference yield:

: 166828-15-5
4,5,6,8-tetra-O-benzyl-1,2-dideoxy-α-D-gluco-oct-1-eno-3-ulopyranose

: 194668-86-5
(S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / BF₃*Et₂O / 20 °C

2: 2percent NaOH / methanol / Ambient temperature

3: 1.) LDA / 1.) THF, -78 deg C to 0 deg C, 2.) Et₂O, MeOH

4: H₂ / Raney-Ni / methanol

5: DBU / toluene / 20 °C

6: 92 percent / Bu₄NN₃ / toluene / 55 °C

With sodium hydroxide; boron trifluoride diethyl etherate; hydrogen; tetrabutylammoniun azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; nickel; In methanol; toluene;
DOI:10.1039/a703063k

Reference yield:

: 194668-79-6
((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-2-yloxy)-acetic acid methyl ester

: 194668-86-5
(S)-2-Azido-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2percent NaOH / methanol / Ambient temperature

2: 1.) LDA / 1.) THF, -78 deg C to 0 deg C, 2.) Et₂O, MeOH

3: H₂ / Raney-Ni / methanol

4: DBU / toluene / 20 °C

5: 92 percent / Bu₄NN₃ / toluene / 55 °C

With sodium hydroxide; hydrogen; tetrabutylammoniun azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; nickel; In methanol; toluene;
DOI:10.1039/a703063k