(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

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Chemical Name:(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid
CAS No.:1054622-71-7
Molecular Formula:C₃₁H₃₅NO₈
Molecular Weight:549.621
Hs Code.:

Synonyms:(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

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Chemical Property of (R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

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Technology Process of (R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

There total 9 articles about (R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid 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:

: 161147-41-7
Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6,7,8-trideoxy-L-glycero-α-D-gluco-oct-7-ynopyranoside

: 1054622-71-7
(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:: With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; at 45 ℃; for 5h;
DOI:10.1021/jo00108a030

Reference yield:

: 83051-88-1
methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 1054622-71-7
(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi, MgBr₂ / 1.) hexane, Et₂O, -5 deg C, 30 min, 2.) -30 deg C to r.t.

2: 74 percent / Bu₄NF / tetrahydrofuran / 0.25 h / Ambient temperature

3: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

4: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

5: pyridine / 3 h / Ambient temperature

6: OsO₄, aq. NaIO₄ / tetrahydrofuran / 5 h / 45 °C

With pyridine; 1.3-propanedithiol; sodium periodate; osmium(VIII) oxide; n-butyllithium; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; magnesium bromide; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo00108a030

Reference yield:

: 103597-18-8
methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside

: 1054622-71-7
(R)-Acetylamino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

2: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

3: pyridine / 3 h / Ambient temperature

4: OsO₄, aq. NaIO₄ / tetrahydrofuran / 5 h / 45 °C

With pyridine; 1.3-propanedithiol; sodium periodate; osmium(VIII) oxide; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo00108a030