4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

Base Information

Chemical Name:4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol
CAS No.:106799-10-4
Molecular Formula:C₂₈H₃₂O₅
Molecular Weight:448.559
Hs Code.:

Synonyms:4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

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Chemical Property of 4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

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Technology Process of 4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

There total 9 articles about 4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol 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: 82.0%

: 106820-43-3
(4R,5R)-5,6-bis(phenylmethoxy)-4-<(phenylmethoxy)methyl>-2-hexen-1-ol

: 106799-10-4
4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate; In dichloromethane; at -20 ℃; for 16h;
DOI:10.1021/ja00241a062

Reference yield:

: 81177-24-4
(S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane

: 106799-10-4
4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / CuI / tetrahydrofuran / 1 h / -78 - 0 °C

2: 93 percent / NaH / tetrahydrofuran / 16 h / 0 - 25 °C

3: 1.) ozone; 2.) dimethyl sulfide; 3.) Ph₃P / 1.) CH₂Cl₂-MeOH, -78 deg C; 2.) CH₂Cl₂-MeOH, -78 to 25 deg C, 3 h; 3.) CH₂Cl₂-MeOH, 25 deg C, 0.5 h

4: 85 percent / benzene / 16 h / Ambient temperature

5: 93 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6: 1.) (-)-diethyltartarate, Ti(O-i-Pr)4, t-BuOOH; 2.) 10percent tartaric acid / 1.) CH₂Cl₂, -20 gradC, 16 h; 2.) CH₂Cl₂, -20 gradC, 1 h; 3.) CH₂Cl₂, 25 gradC, 1 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; dimethylsulfide; sodium hydride; diisobutylaluminium hydride; ozone; tartaric acid; (-)-diethyl tartrate; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja00222a028

Reference yield:

: 106799-09-1
(4R,5R)-5,6-bis(phenylmethoxy)-4-<(phenylmethoxy)methyl>-2-hexyn-1-ol

: 106799-10-4
4,5-anhydro-3-deoxy-3-<(phenylmethoxy)methyl>-1,2-bis-O-(phenylmethyl)galactitol

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / Red-Al / toluene; diethyl ether / 3 h / Ambient temperature

2: 1.) (-)-diethyltartarate, Ti(O-i-Pr)4, t-BuOOH; 2.) 10percent tartaric acid / 1.) CH₂Cl₂, -20 gradC, 16 h; 2.) CH₂Cl₂, -20 gradC, 1 h; 3.) CH₂Cl₂, 25 gradC, 1 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tartaric acid; (-)-diethyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene;
DOI:10.1021/ja00222a028