(2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

Base Information

Chemical Name:(2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran
CAS No.:172995-73-2
Molecular Formula:C₂₁H₃₂O₅
Molecular Weight:364.482
Hs Code.:

Synonyms:(2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

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Chemical Property of (2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

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Technology Process of (2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

There total 5 articles about (2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran 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: 95.0%

: 172995-86-7
(2R,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-methoxycarbonylmethyltetrahydropyran

: 149-73-5
trimethyl orthoformate

: 172995-73-2
(2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; for 1.5h; Ambient temperature;
DOI:10.1016/0040-4020(95)00905-1

Reference yield:

: 90093-98-4
(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

: 172995-73-2
(2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 17 h

2: 76 percent / 1N aq. H₂SO₄ / dioxane / 3.5 h / 50 °C

3: 92 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) n-BuLi, i-Pr₂NH / 1.) THF, 30 min, 2.) THF, from -80 deg C to RT, 19 h

5: 95 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 1.5 h / Ambient temperature

With n-butyllithium; 3 A molecular sieve; sulfuric acid; camphor-10-sulfonic acid; sodium hydride; diisopropylamine; pyridinium chlorochromate; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1016/0040-4020(95)00905-1

Reference yield:

: 144606-47-3
(2R,4S,5S,6S)-7-benzyloxy-5-hydroxy-2,4,6-trimethylheptanoic acid δ-lactone

: 172995-73-2
(2S,3R,5S,6S)-6-<(2S)-benzyloxyprop-2-yl>-3,5-dimethyl-2-methoxy-2-methoxycarbonylmethyltetrahydropyran

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) n-BuLi, i-Pr₂NH / 1.) THF, 30 min, 2.) THF, from -80 deg C to RT, 19 h

2: 95 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 1.5 h / Ambient temperature

With n-butyllithium; camphor-10-sulfonic acid; diisopropylamine; In methanol; dichloromethane;
DOI:10.1016/0040-4020(95)00905-1