3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Base Information

Chemical Name:3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside
CAS No.:236388-62-8
Molecular Formula:C₅₈H₇₉NO₈
Molecular Weight:918.267
Hs Code.:

Synonyms:3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

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Chemical Property of 3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

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Technology Process of 3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

There total 5 articles about 3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside 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:

: 765-13-9
pentadec-1-yne

: 236388-59-3
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitose

: 236388-62-8
3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

: 3'(S)-N-(tert-butoxycarbonylamino)-4'(S)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Guidance literature:: With n-butyllithium; 4 Angstroem MS; In tetrahydrofuran; hexane; at -50 ℃; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/jo990398l

Reference yield:

: 144542-40-5
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol

: 236388-62-8
3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / (COCl)2, DMSO, DIPEA / CH₂Cl₂ / -78 - 0 °C

2: n-BuLi, 4 Angstroem MS / tetrahydrofuran; hexane / -50 °C

With n-butyllithium; oxalyl dichloride; 4 Angstroem MS; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo990398l

Reference yield:

: [1-Hydroxymethyl-3-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester

: 236388-62-8
3'(S)-N-(tert-butoxycarbonylamino)-4'(R)-nonadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / pyridine / 14 h / Ambient temperature

2: 90 percent / MeONa / methanol / 15 h / Ambient temperature

3: 90 percent / (COCl)2, DMSO, DIPEA / CH₂Cl₂ / -78 - 0 °C

4: n-BuLi, 4 Angstroem MS / tetrahydrofuran; hexane / -50 °C

With n-butyllithium; oxalyl dichloride; 4 Angstroem MS; sodium methylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane;
DOI:10.1021/jo990398l