3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

Base Information

Chemical Name:3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal
CAS No.:129986-40-9
Molecular Formula:C₆₀H₁₁₈O₁₂SSi₅
Molecular Weight:1204.08
Hs Code.:

3,5-O-<bis(1,1-dimethylethyl)silylene>-4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

Synonyms:3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

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Chemical Property of 3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

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Technology Process of 3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

There total 20 articles about 3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal 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: 96.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 129986-39-6
C₅₄H₁₀₄O₁₂SSi₄

: 129986-40-9
3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/ja00175a038

Reference yield:

: 129986-21-6
<2R,3S,4S>-2,4-O--3-methyl-5-methylene-1,2,4-hexanetriol

: 129986-40-9
3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

3: 1.) Me₃Al / 1.) THF, toluene, RT, 15 min, 2.) 0 deg C, 2.25 h

4: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.83 h / Ambient temperature

5: 70 percent / trityl perchlorate / toluene / 1.42 h / -8 - -5 °C

6: 95 percent / LiBr / tetrahydrofuran / 0.67 h / -78 °C

7: 86 percent / H₂O, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂ / 2.5 h / Ambient temperature

8: 1.) magnesium / 1.) THF, 40 deg C, 1 h, 2.) a) -40 deg C, 20 min, b) -25 deg C, 14.5 h

9: 1.) n-BuLi / 1.) THF, hexane, from -50 to -40 deg C, 3 min, 2.) -10 deg C, 1.6 h

10: 96 percent / N-methylmorpholine N-oxide monohydrate, aq. OsO₄ / tetrahydrofuran / 22 h

11: 87 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

12: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; water; trimethylaluminum; triphenylmethyl perchlorate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00175a038

Reference yield:

: 129986-33-0
2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranose acetate

: 129986-40-9
3,5-O--4,9,10,11,12-pentadeoxy-6-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-4-methyl-2,8-di-C-methyl-12-(phenylsulfonyl)-2,7,8-tris-O-(triethylsilyl)-D-xylo-L-gulo-dodecanal

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / trityl perchlorate / toluene / 1.42 h / -8 - -5 °C

2: 95 percent / LiBr / tetrahydrofuran / 0.67 h / -78 °C

3: 86 percent / H₂O, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂ / 2.5 h / Ambient temperature

4: 1.) magnesium / 1.) THF, 40 deg C, 1 h, 2.) a) -40 deg C, 20 min, b) -25 deg C, 14.5 h

5: 1.) n-BuLi / 1.) THF, hexane, from -50 to -40 deg C, 3 min, 2.) -10 deg C, 1.6 h

6: 96 percent / N-methylmorpholine N-oxide monohydrate, aq. OsO₄ / tetrahydrofuran / 22 h

7: 87 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

8: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; water; triphenylmethyl perchlorate; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00175a038