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

Base Information

• Chemical Name: (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one
• CAS No.: 884345-68-0
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• Mol file: 884345-68-0.mol

Synonyms:

Chemical Property of (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one

There total 10 articles about (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one 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:

(S)-1-benzyloxyhept-6-en-3-ol (884345-81-7) → (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one (884345-68-0)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; borane-THF; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 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:

(S)-1-benzyloxy-3-tert-butyldimethylsilyloxyhept-6-ene (884345-65-7) → (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one (884345-68-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: BH₃*THF

1.2: 86 percent / H₂O₂; NaOH

2.1: (COCl)2; DMSO; Et₃N

3.1: Zn

4.1: (COCl)2; DMSO; Et₃N

5.1: TBAF

6.1: 99 percent / camphor sulfonic acid; 4 Angstroem molecular sieves / benzene

7.1: mCPBA

8.1: Dess-Martin periodinane

With borane-THF; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In benzene; 2.1: Swern oxidation / 4.1: Swern oxidation / 8.1: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2006.01.097

Reference yield:

(S)-7-benzyloxy-5-tert-butyldimethylsilyloxyheptanal → (2S,6S)-6-(2-Benzyloxy-ethyl)-2-(1,1-dimethyl-allyl)-2-methoxy-dihydro-pyran-3-one (884345-68-0)

Guidance literature:

Multi-step reaction with 6 steps

1: Zn

2: (COCl)2; DMSO; Et₃N

3: TBAF

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

5: mCPBA

6: Dess-Martin periodinane

With oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In benzene; 2: Swern oxidation / 6: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2006.01.097

upstream raw materials:

(S)-1-benzyloxyhept-6-en-3-ol

2-(2-benzyloxy-ethyl)-6-(1,1-dimethyl-allyl)-3,4-dihydro-2H-pyran

(S)-1-benzyloxy-3-tert-butyldimethylsilyloxyhept-6-ene

(8S)-10-benzyloxy-8-hydroxy-3,3-dimethyldec-1-en-4-one

Downstream raw materials:

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

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