(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran
CAS No.:126394-32-9
Molecular Formula:C₂₂H₃₄O₄
Molecular Weight:362.51
Hs Code.:

Synonyms:(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

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Chemical Property of (2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

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Technology Process of (2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

There total 20 articles about (2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran 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: 100.0%

: 126394-31-8
(R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde

: 107-21-1
ethylene glycol

: 126394-32-9
(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 1.5h; Heating; Dean-Stark apparatus;
DOI:10.1248/cpb.37.1698

Reference yield:

: 81470-77-1,98102-72-8,100760-30-3,115181-74-3,133006-91-4,135211-99-3,138124-14-8,145514-09-6
(2S,3R,4S)-1-benzyloxy-3,5-isopropylidenedioxy-2,4-dimethylpentane

: 126394-32-9
(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 16 steps

1: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

3: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

4: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

5: 97 percent / tetrahydrofuran / 3 h / -40 °C

6: 1) O₃, 2) NaBH₄ / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, MeOH, -78 deg C, 15 min

7: 94 percent / Et₃N / toluene / 2 h / 0 °C

8: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature

9: K₂CO₃ / methanol; H₂O / 1 h

10: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature

11: 83 percent / CSA / CH₂Cl₂ / 0.33 h / 0 °C

12: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

13: 28 percent / (Ph₃P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube

14: 100 percent / DDQ / CH₂Cl₂; H₂O

15: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

16: 100 percent / p-TsOH / benzene / 1.5 h / Heating; Dean-Stark apparatus

With hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; benzene;
DOI:10.1248/cpb.37.1698

Reference yield:

: 81520-10-7
(2S,3S,4S)-5-Benzyloxy-2,4-dimethylpentan-1,3-diol

: 126394-32-9
(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 17 steps

1: CSA / acetone / 0.5 h / Ambient temperature

2: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

4: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

5: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

6: 97 percent / tetrahydrofuran / 3 h / -40 °C

7: 1) O₃, 2) NaBH₄ / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, MeOH, -78 deg C, 15 min

8: 94 percent / Et₃N / toluene / 2 h / 0 °C

9: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature

10: K₂CO₃ / methanol; H₂O / 1 h

11: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature

12: 83 percent / CSA / CH₂Cl₂ / 0.33 h / 0 °C

13: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

14: 28 percent / (Ph₃P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube

15: 100 percent / DDQ / CH₂Cl₂; H₂O

16: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

17: 100 percent / p-TsOH / benzene / 1.5 h / Heating; Dean-Stark apparatus

With hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; toluene; acetonitrile; benzene;
DOI:10.1248/cpb.37.1698