8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one

Base Information

• Chemical Name: 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one
• CAS No.: 251089-84-6
• Molecular Formula: C₅₅H₉₀N₂O₈S₂Si₃
• Molecular Weight: 1055.72

Synonyms:8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one

Chemical Property of 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one

There total 24 articles about 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-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: 64.0%

tert-Butyl-{(4E,6E,8E)-(R)-10-[(4S,5S,6R)-6-((Z)-3-iodo-1-methyl-propenyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-deca-4,6,8-trienyloxy}-dimethyl-silane (251089-67-5) + 8-benzenesulfonylmethyl-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one (251089-55-1) → 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one (251089-84-6)

Guidance literature:

8-benzenesulfonylmethyl-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

tert-Butyl-{(4E,6E,8E)-(R)-10-[(4S,5S,6R)-6-((Z)-3-iodo-1-methyl-propenyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-deca-4,6,8-trienyloxy}-dimethyl-silane; In tetrahydrofuran; at -78 ℃; for 1.5h; Further stages.;

DOI:10.1021/jo991958j

Reference yield:

tert-Butyl-((E)-(R)-5-iodo-3-methoxy-pent-4-enyloxy)-dimethyl-silane (251089-62-0) → 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one (251089-84-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Pd(CH₃CN)2Cl₂

2: (COCl)2; Et₃N; DMSO

3: 85 percent / KHMDS / tetrahydrofuran; toluene / -78 - 20 °C

4: 93 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

5: 78 percent / 2,6-lutidine; LiCl; MeSO₂Cl / dimethylformamide / 1 h / 20 °C

6: NaI; 2,6-di(tert-butyl)-4-methylpyridine / acetone

7: NaHMDS

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; sodium iodide; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Stille coupling / 2: Swern oxidation;

DOI:10.1021/ol991049g

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 8-(1-benzenesulfonyl-4-{6-[10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-deca-2,4,6-trienyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one (251089-84-6)

Guidance literature:

Multi-step reaction with 8 steps

1.2: 96 percent / I₂ / CH₂Cl₂

2.1: Pd(CH₃CN)2Cl₂

3.1: (COCl)2; Et₃N; DMSO

4.1: 85 percent / KHMDS / tetrahydrofuran; toluene / -78 - 20 °C

5.1: 93 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

6.1: 78 percent / 2,6-lutidine; LiCl; MeSO₂Cl / dimethylformamide / 1 h / 20 °C

7.1: NaI; 2,6-di(tert-butyl)-4-methylpyridine / acetone

8.1: NaHMDS

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; sodium iodide; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 2.1: Stille coupling / 3.1: Swern oxidation;

DOI:10.1021/ol991049g

upstream raw materials:

tert-Butyl-{(4E,6E,8E)-(R)-10-[(4S,5S,6R)-6-((Z)-3-iodo-1-methyl-propenyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-deca-4,6,8-trienyloxy}-dimethyl-silane

8-benzenesulfonylmethyl-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one

t-butyldimethylsiyl triflate

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol

Downstream raw materials:

C₃₈H₅₁N₃SO₈C₂H₄O

(+)-thiazinotrienomycin E

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