(2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:114825-98-8
Molecular Formula:C₂₄H₃₈O₆Si
Molecular Weight:450.648
Hs Code.:

Synonyms:(2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 9 articles about (2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

: 104265-72-7
(3R,4S)-4-Benzyloxymethoxy-2-methyl-pent-1-en-3-ol

: 114825-98-8
(2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 50percent NaOH / Bu₄NHSO₄ / benzene / 10 °C

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to 25 deg C

3: diethyl ether / -78 °C

4: CF₃CO₂H / benzene / Heating

6: 1.) BH₃*THF, 2.) H₂O₂, aq OH^(1-) / 1.) THF, -78 deg C to 0 deg C, 2.) 0 deg C to 25 deg C

7: i-Pr₂NEt / CH₂Cl₂ / 0 °C

8: BF₃*Et₂O, EtSH / CH₂Cl₂ / 0 °C

9: PCC, 3 Angstroem molecular sieves / CH₂Cl₂

With sodium hydroxide; borane-THF; dimethylsulfide; 3 A molecular sieve; boron trifluoride diethyl etherate; hydroxide; dihydrogen peroxide; ozone; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; ethanethiol; tetra(n-butyl)ammonium hydrogensulfate; In diethyl ether; dichloromethane; benzene;
DOI:10.1016/S0040-4039(00)95561-8

Reference yield:

: (2S,3S,4S,5R,6R)-3-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-((S)-1-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

: 114825-98-8
(2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane; Yield given;
DOI:10.1016/S0040-4039(00)95561-8

Reference yield:

: 114825-97-7
(5S,6S)-5-((S)-1-Benzyloxymethoxy-ethyl)-6-((E)-3-benzyloxy-propenyl)-6-methyl-[1,4]dioxan-2-one

: 114825-98-8
(2S,3S,4S,5R,6R)-6-Acetyl-3-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

2: 1.) BH₃*THF, 2.) H₂O₂, aq OH^(1-) / 1.) THF, -78 deg C to 0 deg C, 2.) 0 deg C to 25 deg C

3: i-Pr₂NEt / CH₂Cl₂ / 0 °C

4: BF₃*Et₂O, EtSH / CH₂Cl₂ / 0 °C

5: PCC, 3 Angstroem molecular sieves / CH₂Cl₂

With borane-THF; 3 A molecular sieve; boron trifluoride diethyl etherate; hydroxide; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; ethanethiol; In dichloromethane;
DOI:10.1016/S0040-4039(00)95561-8