methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose

Base Information

• Chemical Name: methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose
• CAS No.: 105539-55-7
• Molecular Formula: C₂₆H₄₀O₅S
• Molecular Weight: 464.667
• Mol file: 105539-55-7.mol

Synonyms:methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose

Chemical Property of methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose

There total 17 articles about methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose 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: 58.0%

methylthiol (74-93-1) + (+/-)-1,5-anhydro-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-D-arabino-L-manno-undec-1-en-ulose (105539-54-6) → methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose (105539-55-7) + (2S,3S,6S)-2-{(R)-1-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethyl}-3-methyl-6-methylsulfanyl-tetrahydro-pyran-4-one (105616-12-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -15 ℃; for 0.75h;

DOI:10.1021/ja00237a037

Reference yield:

1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene (72486-93-2) → methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose (105539-55-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 30 min

2: 91 percent / LiAlH₄ / diethyl ether / -78 °C

3: 92 percent / p-TsOH*H₂O / 10 h / Ambient temperature

4: 1) BF₃*THF, 2) 30percent H₂O₂, NaOH / 1) THF, 0 deg C, 30 min, 2) THF, 12 h, RT

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 10 min, 2) CH₂Cl₂, -78 deg C to RT

6: 86 percent / NaBH₄ / methanol / 0.33 h / -25 °C

7: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - 0 °C

8: 87 percent / d,l-10-camphorsulfonic acid*H₂O / 6 h / Ambient temperature

9: 83 percent / NBS, H₂O / acetone / 0.03 h / -25 °C

10: 57 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -78 °C

11: Li di-sec-butylborohydride / tetrahydrofuran / 0.08 h / -78 °C

12: 1) m-chloroperbenzoic acid, 2) Et₃N, Me₂S / 1) toluene, 0 deg C, 10 min, 3) toluene, reflux,

13: 58 percent / n-Bu₄NF / tetrahydrofuran / 0.75 h / -15 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; dimethylsulfide; lithium di-n-2-methyl-1-propylborohydride; boron trifluoride diethyl etherate; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;

DOI:10.1021/ja00237a037

Reference yield:

3-(benzyloxy)-2-methylpropanal (74130-31-7,79026-61-2,79027-28-4,73814-73-0) → methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-arabino-β-L-manno-undecopyranosid-3-ulose (105539-55-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 30 min

2: 91 percent / LiAlH₄ / diethyl ether / -78 °C

3: 92 percent / p-TsOH*H₂O / 10 h / Ambient temperature

4: 1) BF₃*THF, 2) 30percent H₂O₂, NaOH / 1) THF, 0 deg C, 30 min, 2) THF, 12 h, RT

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 10 min, 2) CH₂Cl₂, -78 deg C to RT

6: 86 percent / NaBH₄ / methanol / 0.33 h / -25 °C

7: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - 0 °C

8: 87 percent / d,l-10-camphorsulfonic acid*H₂O / 6 h / Ambient temperature

9: 83 percent / NBS, H₂O / acetone / 0.03 h / -25 °C

10: 57 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -78 °C

11: Li di-sec-butylborohydride / tetrahydrofuran / 0.08 h / -78 °C

12: 1) m-chloroperbenzoic acid, 2) Et₃N, Me₂S / 1) toluene, 0 deg C, 10 min, 3) toluene, reflux,

13: 58 percent / n-Bu₄NF / tetrahydrofuran / 0.75 h / -15 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; dimethylsulfide; lithium di-n-2-methyl-1-propylborohydride; boron trifluoride diethyl etherate; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;

DOI:10.1021/ja00237a037

upstream raw materials:

methylthiol

(+/-)-1,5-anhydro-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-D-arabino-L-manno-undec-1-en-ulose

1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene

3-(benzyloxy)-2-methylpropanal

Downstream raw materials:

methyl (+/-)-2,4,6,8,10-pentadeoxy-4,6,8,10-tetramethyl-3-O-methyl-7,9-O-(1-methylethylidene)-11-O-(phenylmethyl)-1-thio-D-manno-β-L-galacto-undecopyranoside

(2R,3R,4S,6R)-2-{(R)-1-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethyl}-3-methyl-6-methylsulfanyl-tetrahydro-pyran-4-ol