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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol
CAS No.:125846-32-4
Molecular Formula:C₅₄H₁₀₆O₁₂SSi₄
Molecular Weight:1091.84
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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

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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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

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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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

There total 18 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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol 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%

: 125846-31-3,130061-23-3
<4R-<4α(1R^*,2R^*,3R^*),5α,6α>>-<1-<2,2-bis(1,1-dimethylethyl)-5-methyl-6-(1-methylethenyl)-1,3-dioxa-2-silacycyclohex-4-yl>-2,3-bis<(triethylsilyl)oxy>-3-methyl-7-(phenylthio)heptyl> 2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyr...

: 125846-32-4
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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; for 22h;
DOI:10.1021/ja00175a038

Reference yield:

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

: 125846-32-4
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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 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:

: 129986-20-5
<2R,3R>-3-hydroxy-N-methoxy-N,2-dimethyl-4-(phenylmethoxy)butanamide

: 125846-32-4
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)-7,8-bis-O-(triethylsilyl)-D-xylo-L-gulo-dodecitol

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) lithium / 1.) Et₂O, from 0 deg C to RT, 14.5 h, 2.) THF, -78 deg C, 40 min

2: 99 percent / methoxydiethylborane, NaBH₄ / tetrahydrofuran; methanol / 4 h / -70 °C

3: 97 percent / 2,6-lutidine / CH₂Cl₂ / 9 h / 65 °C

4: 80 percent / Ca/NH₃ / tetrahydrofuran / 0.4 h / -63 - -45 °C

5: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

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

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

9: 70 percent / trityl perchlorate / toluene / 1.42 h / -8 - -5 °C

10: 95 percent / LiBr / tetrahydrofuran / 0.67 h / -78 °C

11: 86 percent / H₂O, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂ / 2.5 h / Ambient temperature

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

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

14: 96 percent / N-methylmorpholine N-oxide monohydrate, aq. OsO₄ / tetrahydrofuran / 22 h

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