{(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane
• CAS No.: 329359-31-1
• Molecular Formula: C₅₅H₇₈O₁₂SSi
• Molecular Weight: 991.369

Synonyms:{(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

Chemical Property of {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

There total 18 articles about {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane 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: 77.0%

sodium benzenesulfonate (873-55-2) + {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-62-8) → {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-31-1)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1002/1521-3773(20010105)40:1<191::AID-ANIE191>3.0.CO;2-C

Reference yield:

(2S,4S)-5-[2-((2S,4R)-5-Benzyloxy-2,4-dihydroxy-pentyl)-[1,3]dithian-2-yl]-4-methoxy-pentane-1,2-diol → {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-31-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Hg(ClO₄)2; CaCO₃ / acetonitrile; H₂O

2.1: HClO₄ / CH₂Cl₂; acetonitrile

3.1: 87 percent / Et₃N / CH₂Cl₂

4.1: 99 percent / imidazole / dimethylformamide

5.1: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

6.1: 90 percent / I₂; PPh₃; imidazole / benzene

7.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C

7.2: 95 percent / tetrahydrofuran / -78 - 0 °C

8.1: 71 percent / Hg(ClO₄)2; CaCO₃ / methanol; H₂O / 0 °C

9.1: NaBH₄ / methanol; CH₂Cl₂

10.1: 94 percent / iPr₂NEt / CH₂Cl₂

11.1: 78 percent / DIBAL / toluene; various solvent(s) / -78 - 0 °C

12.1: 96 percent / I₂; PPh₃; imidazole / benzene; acetonitrile

13.1: 77 percent / dimethylformamide / 50 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; perchloric acid; mercury(II) perchlorate; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010105)40:1<191::AID-ANIE191>3.0.CO;2-C

Reference yield:

(S)-4-((S)-3-{2-[(2S,4R)-5-Benzyloxy-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentyl]-[1,3]dithian-2-yl}-2-methoxy-propyl)-2,2-dimethyl-[1,3]dioxolane (201275-41-4) → {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-31-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 85 percent / HCl / methanol

2.1: Hg(ClO₄)2; CaCO₃ / acetonitrile; H₂O

3.1: HClO₄ / CH₂Cl₂; acetonitrile

4.1: 87 percent / Et₃N / CH₂Cl₂

5.1: 99 percent / imidazole / dimethylformamide

6.1: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

7.1: 90 percent / I₂; PPh₃; imidazole / benzene

8.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C

8.2: 95 percent / tetrahydrofuran / -78 - 0 °C

9.1: 71 percent / Hg(ClO₄)2; CaCO₃ / methanol; H₂O / 0 °C

10.1: NaBH₄ / methanol; CH₂Cl₂

11.1: 94 percent / iPr₂NEt / CH₂Cl₂

12.1: 78 percent / DIBAL / toluene; various solvent(s) / -78 - 0 °C

13.1: 96 percent / I₂; PPh₃; imidazole / benzene; acetonitrile

14.1: 77 percent / dimethylformamide / 50 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; perchloric acid; mercury(II) perchlorate; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010105)40:1<191::AID-ANIE191>3.0.CO;2-C

upstream raw materials:

sodium benzenesulfonate

{(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

tert-butyldimethylsilyl chloride

(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol

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