(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

Base Information

Chemical Name:(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid
CAS No.:767344-28-5
Molecular Formula:C₄₄H₄₃NO₈
Molecular Weight:713.827
Hs Code.:

Synonyms:(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

There total 9 articles about (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic 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: 64.0%

: 767344-26-3
[(R)-1-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

: 767344-28-5
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: [(R)-1-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester; With acetic anhydride; acetic acid; zinc(II) chloride; at 20 ℃;

With hydrogenchloride; In methanol; at 20 ℃;

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; Further stages.;
DOI:10.1039/b705750d

Reference yield:

: [(R)-1-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

: 767344-28-5
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 5h;
DOI:10.1021/ol048750r

Reference yield:

: 113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9
2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

: 767344-28-5
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[(R)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 72 percent / Ti(OiPr)4 / CH₂Cl₂ / 4 h / 20 °C

2.1: CH₂Cl₂; diethyl ether / 1.33 h / -78 °C

2.2: HCl; methanol / dioxane / 0.5 h / 20 °C

2.3: 75 percent / DIPEA / CH₂Cl₂; dioxane / 2.5 h

3.1: AcOH; Ac₂O; ZnCl₂ / 20 °C

3.2: HCl / methanol / 20 °C

3.3: 64 percent / iodobenzene diacetate; 2,2,6,6-tetramethylpiperidine-1-oxyl / CH₂Cl₂; H₂O / 20 °C

With titanium(IV) isopropylate; acetic anhydride; acetic acid; zinc(II) chloride; In diethyl ether; dichloromethane;
DOI:10.1039/b705750d