(2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester
• CAS No.: 326494-39-7
• Molecular Formula: C₄₆H₇₆O₁₃Si₂
• Molecular Weight: 893.273

Synonyms:(2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester

Chemical Property of (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester

Chemical Property:

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Technology Process of (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester

There total 20 articles about (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl 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:

1,1-dimethoxycyclopentane (931-94-2) → (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester (326494-39-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 87 percent / p-TsOH / benzene / 20 °C

2.1: O₃ / methanol / -78 °C

2.2: Me₂S / methanol

3.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

4.1: CH₂Cl₂ / 20 °C

5.1: 88 percent / H₂ / Pd/C / methanol / 20 °C

6.1: O₃ / methanol / -78 °C

6.2: Me₂S / methanol

7.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

8.1: CH₂Cl₂ / 20 °C

9.1: 94 percent / TBAF / tetrahydrofuran / 0 °C

10.1: 93 percent / H₂ / Lindlar catalyst / methanol / 20 °C

11.1: O₃ / methanol / -78 °C

11.2: Me₂S / methanol

12.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

13.1: CH₂Cl₂ / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; ozone; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

(3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one → (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester (326494-39-7)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 75 percent / diethyl ether / -78 °C

2.1: 80 percent / montmorillonite K 10; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

3.1: BuLi; molecular sieves 4 Angstroem / tetrahydrofuran / -78 °C

4.1: 83 percent / Red-Al / diethyl ether / -15 °C

5.1: O₃ / methanol / -78 °C

5.2: Me₂S / methanol

6.1: toluene / -78 °C

7.1: 87 percent / p-TsOH / benzene / 20 °C

8.1: O₃ / methanol / -78 °C

8.2: Me₂S / methanol

9.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

10.1: CH₂Cl₂ / 20 °C

11.1: 88 percent / H₂ / Pd/C / methanol / 20 °C

12.1: O₃ / methanol / -78 °C

12.2: Me₂S / methanol

13.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

14.1: CH₂Cl₂ / 20 °C

15.1: 94 percent / TBAF / tetrahydrofuran / 0 °C

16.1: 93 percent / H₂ / Lindlar catalyst / methanol / 20 °C

17.1: O₃ / methanol / -78 °C

17.2: Me₂S / methanol

18.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

19.1: CH₂Cl₂ / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 4 A molecular sieve; Montmorillonite K 10; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; tert-butyl alcohol; benzene; 3.1: acetal <1,2> Wittig rearrangement;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

(3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-ol → (2S,3S)-2-[(2R,3R,4S,5S)-5-Benzoyloxymethyl-2-tert-butoxycarbonyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid di-tert-butyl ester (326494-39-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 80 percent / montmorillonite K 10; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

2.1: BuLi; molecular sieves 4 Angstroem / tetrahydrofuran / -78 °C

3.1: 83 percent / Red-Al / diethyl ether / -15 °C

4.1: O₃ / methanol / -78 °C

4.2: Me₂S / methanol

5.1: toluene / -78 °C

6.1: 87 percent / p-TsOH / benzene / 20 °C

7.1: O₃ / methanol / -78 °C

7.2: Me₂S / methanol

8.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

9.1: CH₂Cl₂ / 20 °C

10.1: 88 percent / H₂ / Pd/C / methanol / 20 °C

11.1: O₃ / methanol / -78 °C

11.2: Me₂S / methanol

12.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

13.1: CH₂Cl₂ / 20 °C

14.1: 94 percent / TBAF / tetrahydrofuran / 0 °C

15.1: 93 percent / H₂ / Lindlar catalyst / methanol / 20 °C

16.1: O₃ / methanol / -78 °C

16.2: Me₂S / methanol

17.1: aq. NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol / 20 °C

18.1: CH₂Cl₂ / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 4 A molecular sieve; Montmorillonite K 10; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; tert-butyl alcohol; benzene; 2.1: acetal <1,2> Wittig rearrangement;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

upstream raw materials:

2-tert-butyl-1,3-diisopropylisourea

1,1-dimethoxycyclopentane

(3R,4S)-4-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-6-trimethylsilanyl-hex-1-en-5-yne-3,4-diol

(2S,3R)-2-[(2R,3R,4S,5S)-5-Benzyloxymethyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-furan-2-yl]-2-trimethylsilanylethynyl-3-vinyl-1,4-dioxa-spiro[4.4]nonane

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