(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

Base Information

Chemical Name:(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol
CAS No.:89726-71-6
Molecular Formula:C₃₄H₅₂O₈SSi
Molecular Weight:648.934
Hs Code.:

(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

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Chemical Property of (4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

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Technology Process of (4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

There total 18 articles about (4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol 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:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2,36562-42-2
L-arabinofuranose

: 89726-71-6,89824-54-4
(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 81 percent / p-TsOH / 48 h / 60 °C

2: 90 percent / dimethoxypropane, p-TsOH / 12 h / Ambient temperature

3: 1.) MeLi / 1.) THF, ether, -78 deg C, 15 min, 2.) THF, ether, from -78 deg C to RT, 45 min

4: 80 percent / toluene / 65 h / 23 °C / Irradiation

5: NaIO₄, OsO₄ / tetrahydrofuran; H₂O / 3 h / 23 °C

6: NaBH₄ / ethanol / 1 h / 23 °C

7: 90 percent / pyridine / 12 h / 23 °C

8: dimethylformamide / 1 h / 0 - 23 °C

9: 75 percent / NaHCO₃, 40percent peracetic acid / CHCl₃ / 10 h / 0 - 23 °C

10: 1.) lithiohexamethyldisilazane / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, hexane, 5 min

With pyridine; peracetic acid; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; dimethoxypropane; methyllithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00222a023

Reference yield:

: 83160-44-5
(3aR,7S,7aR)-7-Allyl-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

: 89726-71-6,89824-54-4
(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: NaIO₄, OsO₄ / tetrahydrofuran; H₂O / 3 h / 23 °C

2: NaBH₄ / ethanol / 1 h / 23 °C

3: 90 percent / pyridine / 12 h / 23 °C

4: dimethylformamide / 1 h / 0 - 23 °C

5: 75 percent / NaHCO₃, 40percent peracetic acid / CHCl₃ / 10 h / 0 - 23 °C

6: 1.) lithiohexamethyldisilazane / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, hexane, 5 min

With pyridine; peracetic acid; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydrogencarbonate; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00222a023

Reference yield:

: 89726-69-2,89824-52-2
2-((3aR,7S,7aR)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethanol

: 89726-71-6,89824-54-4
(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / pyridine / 12 h / 23 °C

2: dimethylformamide / 1 h / 0 - 23 °C

3: 75 percent / NaHCO₃, 40percent peracetic acid / CHCl₃ / 10 h / 0 - 23 °C

4: 1.) lithiohexamethyldisilazane / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, hexane, 5 min

With pyridine; peracetic acid; sodium hydrogencarbonate; lithium hexamethyldisilazane; In chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00222a023