(1''R,4''R)-(+)-ascofuranol

Base Information

Chemical Name:(1''R,4''R)-(+)-ascofuranol
CAS No.:99529-63-2
Molecular Formula:C₂₃H₃₁ClO₅
Molecular Weight:422.949
Hs Code.:

Synonyms:(1''R,4''R)-(+)-ascofuranol

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Chemical Property of (1''R,4''R)-(+)-ascofuranol

Chemical Property:

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Technology Process of (1''R,4''R)-(+)-ascofuranol

There total 11 articles about (1''R,4''R)-(+)-ascofuranol 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: 91.0%

: 99529-61-0
(2'E,6'E,1''R,4''R)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde

: 99529-63-2,99529-62-1
(1''R,4''R)-(+)-ascofuranol

Guidance literature:: With sodium methylate; In methanol; for 24h; Ambient temperature;

Reference yield: 70.0%

: 99529-61-0
(2'E,6'E,1''R,4''R)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde

: 99529-63-2,99529-62-1
(1''R,4''R)-(+)-ascofuranol

Guidance literature:: With hydrogen fluoride; In water; acetonitrile; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96657-8

Reference yield:

: 99477-55-1,99529-54-1,99529-56-3,99529-57-4
(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

: 99529-63-2,99529-62-1
(1''R,4''R)-(+)-ascofuranol

Guidance literature:: Multi-step reaction with 10 steps

1: 4.97 g / 14 h / 80 °C

2: 74 percent / Et₃N, HSiCl₃ / benzene / 144 h / Ambient temperature

3: 98.5 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

4: 93.8 percent / K₂CO₃ / methanol; H₂O / 48 h / Ambient temperature

5: 1.51 g / n-BuLi, Ph₃CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C

6: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C

7: 49.3 percent / CaCO₃, NCS / H₂O; dimethylformamide / Ambient temperature

8: 67.7 percent / DBU / tetrahydrofuran / 6 h / Heating

9: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.

10: 70 percent / HF / acetonitrile; H₂O / 1 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; trichlorosilane; hydrogen fluoride; ethylmagnesium bromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; calcium carbonate; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)96657-8