tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

Base Information

Chemical Name:tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate
CAS No.:143949-30-8
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

Synonyms:tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

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Chemical Property of tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

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Technology Process of tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

There total 4 articles about tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate 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: 96.0%

: 143949-29-5
tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate

: 143949-30-8
tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

Guidance literature:: With trimethylamine-N-oxide; osmium(VIII) oxide; In water; acetone; at 20 ℃; for 15h;
DOI:10.1016/S0040-4039(00)61322-9

Reference yield:

: 144016-17-1
(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

: 143949-30-8
tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 95percent H₂SO₄ / CH₂Cl₂ / 48 h / Ambient temperature

2: 1.) NaH / 1.) mineral oil, THF, 0 deg C, 20 min, 2.) mineral oil, THF, 0 deg C, 3 h

3: 96 percent / OsO₄, Me₃NO*2H₂O, water / acetone / 15 h / Ambient temperature

With osmium(VIII) oxide; trimethylamine-N-oxide; sulfuric acid; water; sodium hydride; In dichloromethane; acetone;
DOI:10.1248/cpb.42.854

Reference yield:

: 127658-15-5
(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

: 143949-30-8
tert-butyl <1R-(1α,2ξ,3ξ,4α,5α,6α)>-3-benzyloxy-5,6-dihydroxybicyclo<2.2.1>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 2.57 g / 2N aq. NaOH / 1,2-dimethoxy-ethane; methanol / 1 h / 0 °C

2: 95percent H₂SO₄ / CH₂Cl₂ / 48 h / Ambient temperature

3: 1.) NaH / 1.) mineral oil, THF, 0 deg C, 20 min, 2.) mineral oil, THF, 0 deg C, 3 h

4: 96 percent / OsO₄, Me₃NO*2H₂O, water / acetone / 15 h / Ambient temperature

With sodium hydroxide; osmium(VIII) oxide; trimethylamine-N-oxide; sulfuric acid; water; sodium hydride; In methanol; 1,2-dimethoxyethane; dichloromethane; acetone;
DOI:10.1248/cpb.42.854