(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane

Base Information

• Chemical Name: (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane
• CAS No.: 228393-98-4
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429
• Mol file: 228393-98-4.mol

Synonyms:(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane

Chemical Property of (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane

There total 5 articles about (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane 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: 87.0%

methyl magnesium iodide (917-64-6) + (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane (199122-41-3) → (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane (228393-98-4)

Guidance literature:

In diethyl ether; benzene; at 70 ℃; for 48h;

DOI:10.1016/0040-4039(96)00289-4

Reference yield:

(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol (156126-13-5) → (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane (228393-98-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / p-TsOH*H₂O / 2 h / Heating

2: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

5: 87 percent / hexane; diethyl ether / 48 h / 70 °C

With sodium perborate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo990010m

Reference yield:

(1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane (199122-31-1) → (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-4-tert-butyloxy-3-hydroxy-2-hydroxymethylbicyclo<3.1.0>hexane (228393-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

2: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

3: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

4: 87 percent / hexane; diethyl ether / 48 h / 70 °C

With sodium perborate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo990010m

upstream raw materials:

methyl magnesium iodide

(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol

(1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

Downstream raw materials:

dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester