(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

Base Information

Chemical Name:(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol
CAS No.:666754-31-0
Molecular Formula:C₂₈H₃₉NO₉Si
Molecular Weight:561.704
Hs Code.:

Synonyms:(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

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Chemical Property of (2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

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Technology Process of (2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

There total 6 articles about (2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol 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: 80.0%

: 666754-30-9
methyl 4(R)-benzoxy-6-(tert-butyldimethylsiloxy)-5(R)-[[N-(phenylmethoxy)carbonyl]amino]hex-2(E)-enoate

: 666754-31-0
(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In dichloromethane; water; for 12h;
DOI:10.3987/com-03-s(p)12

Reference yield:

: N-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-benzamide

: 666754-31-0
(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

Guidance literature:: Multi-step reaction with 6 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

1.2: 75 percent / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / 20 °C

3.1: 75 percent / K₂CO₃ / Pd(PPh₃)4 / acetonitrile / 24 h / Heating

4.1: 85 percent / NaHCO₃ / CH₂Cl₂; H₂O / 4 h / 20 °C

5.1: O₃ / ethanol / -78 °C

5.2: 87 percent / LiCl; iPr₂NEt / acetonitrile / 3 h

6.1: 80 percent / N-methylmorpholine N-oxide; OsO₄ / CH₂Cl₂; H₂O / 12 h

With dmap; osmium(VIII) oxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In pyridine; ethanol; dichloromethane; water; acetonitrile;
DOI:10.3987/com-03-s(p)12

Reference yield:

: 666754-26-3
(-)-N-[(R)-2-hydroxy-1-(tert-butyldimethylsilanyloxymethyl)but-3-enyl]benzamide

: 666754-31-0
(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / 20 °C

2.1: 75 percent / K₂CO₃ / Pd(PPh₃)4 / acetonitrile / 24 h / Heating

3.1: 85 percent / NaHCO₃ / CH₂Cl₂; H₂O / 4 h / 20 °C

4.1: O₃ / ethanol / -78 °C

4.2: 87 percent / LiCl; iPr₂NEt / acetonitrile / 3 h

5.1: 80 percent / N-methylmorpholine N-oxide; OsO₄ / CH₂Cl₂; H₂O / 12 h

With dmap; osmium(VIII) oxide; sodium hydrogencarbonate; potassium carbonate; ozone; 4-methylmorpholine N-oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In pyridine; ethanol; dichloromethane; water; acetonitrile;
DOI:10.3987/com-03-s(p)12