Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside

Base Information

Chemical Name:Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside
CAS No.:180776-29-8
Molecular Formula:C21H29NO6
Molecular Weight:391.464
Hs Code.:
Mol file:180776-29-8.mol

Synonyms:Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside

Suppliers and Price of Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Total 2 raw suppliers

Chemical Property of Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

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Technology Process of Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside

There total 10 articles about Methyl 5,6,7,8,9-pentadeoxy-2,3-O-(1-methylethylidene)-6-[[(phenylmethoxy)carbonyl]amino]-alpha-L-talo-non-8-enofuranoside 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: 85.0%

: 180776-28-7
(S)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-pent-4-enoic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 180776-29-8
[(S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: (S)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-pent-4-enoic acid; With diphenyl phosphoryl azide; In toluene; at 20 ℃;

benzyl alcohol; In toluene;

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 180776-29-8
[(S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 23 deg C, 40 min, 2.) THF, 0 deg C (5 min), -> 23 deg C (30 min)

2: 99 percent / H₂ / Pd/C / ethyl acetate / 9 h

3: 100 percent / aq. LiOH / tetrahydrofuran / 12 h / 23 °C

4: 1.) Et₃N, trimethylacetyl chloride / 1.) THF, -15 deg C (15 min), -> 0 deg C (20 min), 2.) THF, -78 deg C, 1 h

5: 1.)lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C (3 h), -> -40 deg C (3 h)

6: 98 percent / aq. LiOH, H₂O₂ / tetrahydrofuran / 1.) 0 deg C , 1 h, 2.) 23 deg C, 3 h

7: 1.) diphenyl phosphorazidate, triethylamine / 1.) toluene, reflux, 2 h, 2.) toluene, reflux, 12 h

With lithium hydroxide; diphenyl phosphoryl azide; hydrogen; dihydrogen peroxide; pivaloyl chloride; sodium hydride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;
DOI:10.1021/jo960670g

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 180776-29-8
[(S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-but-3-enyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent / cuprous sulfate, conc. sulfuric acid / 48 h / 40 °C

2: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 2 h / -60 °C

3: 1.) NaH / 1.) THF, 23 deg C, 40 min, 2.) THF, 0 deg C (5 min), -> 23 deg C (30 min)

4: 99 percent / H₂ / Pd/C / ethyl acetate / 9 h

5: 100 percent / aq. LiOH / tetrahydrofuran / 12 h / 23 °C

6: 1.) Et₃N, trimethylacetyl chloride / 1.) THF, -15 deg C (15 min), -> 0 deg C (20 min), 2.) THF, -78 deg C, 1 h

7: 1.)lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C (3 h), -> -40 deg C (3 h)

8: 98 percent / aq. LiOH, H₂O₂ / tetrahydrofuran / 1.) 0 deg C , 1 h, 2.) 23 deg C, 3 h

9: 1.) diphenyl phosphorazidate, triethylamine / 1.) toluene, reflux, 2 h, 2.) toluene, reflux, 12 h

With lithium hydroxide; copper(I) sulfate; oxalyl dichloride; sulfuric acid; diphenyl phosphoryl azide; hydrogen; dihydrogen peroxide; pivaloyl chloride; sodium hydride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jo960670g