(4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

Base Information

Chemical Name:(4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester
CAS No.:141692-89-9
Molecular Formula:C₅₇H₈₈N₂O₉
Molecular Weight:945.334
Hs Code.:

Synonyms:(4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

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Chemical Property of (4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

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Technology Process of (4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

There total 9 articles about (4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic 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: 66.0%

: 141692-88-8
(4S,5R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-5-((2R,4S,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-pentanoic acid benzyl ester

: 141692-89-9
(4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

Guidance literature:: With water; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1016/S0040-4039(00)74161-X

Reference yield:

: 101516-69-2
1,4,6-tri-O-acetyl-2-azido-2,3-dideoxy-3-nitro-α-D-glucopyranose

: 141692-89-9
(4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / Pd/C / methanol / 3750.3 Torr

2: H₂ / Pd/C / methanol / 3750.3 Torr

3: 98 percent / NaOMe / methanol / 16 h

4: 1) 32 percent HCl, 2) Et(i-Pr)2N / 1) THF/H₂O, 0 to 25 deg C, 14 h, 2) DMF, 0 to 25 deg C, 20 h

5: 83 percent / PTSH / dimethylformamide / 0.33 h / 75 °C / vacuum

6: 84 percent / benzene / 1.5 h / Heating

7: 90 percent / H₂ / ((C₆H₅)3P)3RhCl / benzene / 72 h

8: 66 percent / TFA/water / CH₂Cl₂ / 0.75 h / 0 °C

With hydrogenchloride; p-toluenesulfonic acid; water; hydrogen; sodium methylate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; Wilkinson's catalyst; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)74161-X

Reference yield:

: ((3R,4R,5S,6R)-4-tert-Butoxycarbonylamino-2,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

: 141692-89-9
(4S,5R,6S,7R)-5-((S)-3-Benzyloxy-tetradecanoylamino)-4-((R)-3-benzyloxy-tetradecanoylamino)-6,7,8-trihydroxy-octanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1) 32 percent HCl, 2) Et(i-Pr)2N / 1) THF/H₂O, 0 to 25 deg C, 14 h, 2) DMF, 0 to 25 deg C, 20 h

2: 83 percent / PTSH / dimethylformamide / 0.33 h / 75 °C / vacuum

3: 84 percent / benzene / 1.5 h / Heating

4: 90 percent / H₂ / ((C₆H₅)3P)3RhCl / benzene / 72 h

5: 66 percent / TFA/water / CH₂Cl₂ / 0.75 h / 0 °C

With hydrogenchloride; p-toluenesulfonic acid; water; hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; Wilkinson's catalyst; In dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)74161-X