(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Base Information

Chemical Name:(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester
CAS No.:182618-39-9
Molecular Formula:C₅₂H₅₇N₃O₁₀
Molecular Weight:884.039
Hs Code.:

(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Synonyms:(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

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Chemical Property of (S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

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Technology Process of (S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

There total 8 articles about (S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl 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: 90.0%

: 182618-30-0
Nα-(9-fluorenylmethoxycarbonyloxy)-β-amino-L-alanine tertbutyl ester

: 182618-25-3
3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid

: 182618-39-9
(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In various solvent(s); for 1h; Ambient temperature;
DOI:10.1002/hlca.19960790602

Reference yield:

: 65729-90-0
1-chloro-N-acetyl-3,4,6-tri-O-benzyl-α-D-glucosamine

: 182618-39-9
(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) Bu₃SnLi, 2.) BuLi / 1.) THF, -78 deg C, 1.5 h, 2.) THF/hexane, -78 deg C -> -65 deg C, 15 min

2: tetrahydrofuran / 1 h

3: 90 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, 1-hydroxybenzotriazol, (i-Pr)2EtN / various solvent(s) / 1 h / Ambient temperature

With n-butyllithium; tri-n-butyltin lithium; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1002/hlca.19960790602

Reference yield:

: 7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4
N-Acetyl-D-glucosamine

: 182618-39-9
(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: BF₃*Et₂O / 2 h / Heating

2: powdered KOH / dioxane / 4 h / Heating

3: 1.) KOt-Bu, 2.) 2M HCl / 1.) DMSO, 100 deg C, 3 h, 2.) acetone, reflux, 30 min

4: SOCl₂ / toluene; CHCl₃ / 0.5 h / 20 °C

5: 1.) Bu₃SnLi, 2.) BuLi / 1.) THF, -78 deg C, 1.5 h, 2.) THF/hexane, -78 deg C -> -65 deg C, 15 min

6: tetrahydrofuran / 1 h

7: 90 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, 1-hydroxybenzotriazol, (i-Pr)2EtN / various solvent(s) / 1 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; n-butyllithium; thionyl chloride; tri-n-butyltin lithium; boron trifluoride diethyl etherate; potassium tert-butylate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; chloroform; toluene;
DOI:10.1002/hlca.19960790602