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

Base Information

Chemical Name:(R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester
CAS No.:1053744-41-4
Molecular Formula:C₃₆H₃₉NO₇
Molecular Weight:597.708
Hs Code.:

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

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

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

There total 10 articles about (R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic 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:

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

: 1053744-41-4
(R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester

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

5: CH₂Cl₂

6: H₂ / Raney nickel / tetrahydrofuran / 20 h

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

Reference yield:

: 161147-39-3
Methyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

: 1053744-41-4
(R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester

Guidance literature:: With hydrogen; nickel; In tetrahydrofuran; for 20h;
DOI:10.1021/jo00108a030

Reference yield:

: 908094-04-2
phenyldiazomethane

: 1053744-41-4
(R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: CH₂Cl₂

2: H₂ / Raney nickel / tetrahydrofuran / 20 h

With hydrogen; nickel; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00108a030