(2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

Base Information

Chemical Name:(2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol
CAS No.:301649-46-7
Molecular Formula:C₂₇H₃₇NO₈S
Molecular Weight:535.659
Hs Code.:

Synonyms:(2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

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Chemical Property of (2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

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Technology Process of (2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

There total 1 articles about (2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol 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: 84.0%

: 175229-12-6
(R)-3-benzyloxy-2-(tert-butoxycarbonylamino)propyl phenyl sulfone

: 22323-80-4
(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 301649-46-7
(2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

Guidance literature:: (R)-3-benzyloxy-2-(tert-butoxycarbonylamino)propyl phenyl sulfone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 4h; Further stages.;
DOI:10.1039/b001721n

Reference yield:

: 301649-46-7
(2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

: (Z)-(2S,5R)-1-Benzyloxy-2-[(tert-butoxycarbonyl)amino]-5,6-isopropylidenedioxyhex-3-ene

: 301649-47-8
(E)-(2S,5R)-1-Benzyloxy-2-[(tert-butoxycarbonyl)amino]-5,6-isopropylidenedioxyhex-3-ene

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃; for 3h;
DOI:10.1039/b001721n

Reference yield:

: 301649-46-7
(2S,5R)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

: 301649-50-3
1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-glucitol

Guidance literature:: Multi-step reaction with 3 steps

1: Na₂HPO₄; Na-Hg / methanol / 3 h / 0 °C

2: osmium tetraoxide; NMO; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

3: 90 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; disodium hydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; water; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Elimination / 2: Oxidation / 3: Substitution;
DOI:10.1039/b001721n