2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

Base Information

Chemical Name:2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide
CAS No.:1425499-45-1
Molecular Formula:C₁₇H₁₉BrO₄
Molecular Weight:367.239
Hs Code.:

Synonyms:2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

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Chemical Property of 2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

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Technology Process of 2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

There total 7 articles about 2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide 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: 68.0%

: 1393710-14-9
2-O-benzoyl-3,4-O-isopropylidene-6-bromo-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

: 1393710-15-0
2-O-benzoyl-3,4-O-isopropylidene-6-bromo-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide

: 1425499-45-1
2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

: 1425499-46-2
2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide

Guidance literature:: With sodium borohydrid; In N,N,N,N,N,N-hexamethylphosphoric triamide; water; at 20 ℃; for 3h;
DOI:10.1016/j.carres.2012.12.010

Reference yield:

: 488-73-3
(+)-proto-quercitol

: 1425499-45-1
2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

Guidance literature:: Multi-step reaction with 7 steps

1.1: camphor-10-sulfonic acid / acetone / 19 h / 20 °C

2.1: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide / 4.5 h / 0 - 20 °C

3.1: pyridinium p-toluenesulfonate / methanol / 23 h / 4 °C

4.1: pyridine / 21 h / 20 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 21 h / 4 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; bromine / tetrachloromethane / 0.5 h / 20 °C

7.1: sodium borohydrid / water; N,N,N,N,N,N-hexamethylphosphoric triamide / 3 h / 20 °C

With pyridine; n-butyllithium; sodium borohydrid; camphor-10-sulfonic acid; bromine; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; dimethyl sulfoxide; acetone; 5.2: |Wittig-Horner Reaction;
DOI:10.1016/j.carres.2012.12.010

Reference yield:

: 1350889-86-9
C₃₀H₂₆O₈

: 1425499-45-1
2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 21 h / 4 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; bromine / tetrachloromethane / 0.5 h / 20 °C

3.1: sodium borohydrid / water; N,N,N,N,N,N-hexamethylphosphoric triamide / 3 h / 20 °C

With n-butyllithium; sodium borohydrid; bromine; sodium hydrogencarbonate; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; 1.2: |Wittig-Horner Reaction;
DOI:10.1016/j.carres.2012.12.010