(2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol
CAS No.:884345-69-1
Molecular Formula:C₂₀H₃₀O₄
Molecular Weight:334.456
Hs Code.:

Synonyms:(2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

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Technology Process of (2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

There total 11 articles about (2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-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: 88.0%

: 884345-68-0
(2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one

: 884345-69-1
(2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

Guidance literature:: With lithium triethylborohydride;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: 884345-81-7
(S)-1-benzyloxyhept-6-en-3-ol

: 884345-69-1
(2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 93 percent / imidazole

2.1: BH₃*THF

2.2: 86 percent / H₂O₂; NaOH

3.1: (COCl)2; DMSO; Et₃N

4.1: Zn

5.1: (COCl)2; DMSO; Et₃N

6.1: TBAF

7.1: 99 percent / camphor sulfonic acid; 4 Angstroem molecular sieves / benzene

8.1: mCPBA

9.1: Dess-Martin periodinane

10.1: 88 percent / LiBHEt₃

With 1H-imidazole; borane-THF; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium triethylborohydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In benzene; 3.1: Swern oxidation / 5.1: Swern oxidation / 9.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

: 884345-84-0
(8S)-10-benzyloxy-8-hydroxy-3,3-dimethyldec-1-en-4-one

: 884345-69-1
(2S,3R,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / camphor sulfonic acid; 4 Angstroem molecular sieves / benzene

2: mCPBA

3: Dess-Martin periodinane

4: 88 percent / LiBHEt₃

With 4 A molecular sieve; camphor-10-sulfonic acid; lithium triethylborohydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In benzene; 3: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2006.01.097